163622-50-2|5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine| Ambeed

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Quality Control of [ 163622-50-2 ] Purity: 95% SDS Specification

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Product Details of [ 163622-50-2 ]

CAS No. :	163622-50-2
Formula :	C₆H₅IN₄
M.W :	260.04
SMILES Code :	NC1=C2C(NC=C2I)=NC=N1
MDL No. :	MFCD13619882
InChI Key :	KLKWCKQHBCUTCL-UHFFFAOYSA-N
Pubchem ID :	9856490

Safety of [ 163622-50-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 163622-50-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	51.01
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.59 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.15
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.97
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.15
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.93
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.82
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.67
Solubility	0.558 mg/ml ; 0.00214 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.98
Solubility	2.74 mg/ml ; 0.0105 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.13
Solubility	0.191 mg/ml ; 0.000736 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.2 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.02

Application In Synthesis of [ 163622-50-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 163622-50-2 ]

[ 163622-50-2 ] Synthesis Path-Downstream 1~35

1
[ 1500-85-2 ]
[ 163622-50-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-iodo-succinimide; In chloroform; for 2.0h;Reflux;	To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.3 g, 9.7 mmol, 1.0 eq) in CHC13 (45 mL) was added NIS (2.18 g, 9.7 mmol, 1.0 eq) at rt. The solution was refluxed for 2 h. The precipitate was filtered and dried in vacuo to give 5-iodo-7H- pyrrolo[2,3-d]pyrimidin-4-ylamine (2.09 g, 83%) as a white solid.
82.51%	With N-iodo-succinimide; In acetonitrile; at 120℃; for 24.0h;	4-Amino-7H-pyrrolo [2,3-d] pyrimidine (0.60 g, 4.47 mmol) was weighedN-iodosuccinimide (1.51 g, 6.71 mmol)Dissolved in 100 ml of acetonitrile,And heated at 120 for 24h.After the reaction is completed, the solvent is evaporated,With dichloromethane mixed with water extraction,The organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography to give 0.96 g of a yellow solid (82.51% yield).
80%	With N-iodo-succinimide; In chloroform; for 2.0h;Reflux;	1.3 g (9.7 mmol) of 7H-pyrrolo[2,3-d]pyrimidino-4-amine were suspended in 30 mL of chloroform and 2.18 g (9.7 mmol) of N-iodosuccinimide were added. The reaction mixture was refluxed for 2 hours, then the precipitated collected by filtration. The product was purified by a silica gel column eluted by DCM/MeOH 95/5, affording 2.02 g (80%) of the title compound.

73%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; for 3.0h;Cooling with ice;	7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.4 g, 3.0 mmol) was dissolved in 10 mL DMF.NIS (0.74 g, 3.3 mmol) was added in portions under ice bath.After the feeding is completed, the ice bath is removed.The reaction was allowed to proceed at room temperature for 3 hours, and the reaction was confirmed to be complete by TLC. 20 mL of water was added to the reaction solution.It was extracted with ethyl acetate (30 mL*3), and the organic phase was washed with 20 mL of brine.Dry over anhydrous sodium sulfate, concentrate,The residue was separated into a pale yellow solid (0.56 g).The yield was 73%.
	With N-iodo-succinimide; In chloroform; for 2.0h;Reflux;	[0820] Example 6: 5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine (I8): . In a 20mL scintillation vial, purchased pyrrolopyrimidine (1g, 7.45mmol) was dissolved in 7mL of chloroform. NIS (2.18g, 9.69mmol) was added and reaction was refluxed for 2 hours. Upon cooling, precipitate was filtered to yield intermediate I8. LC-MS (ES+) calcd for C6H5IN4 (M+H)+ 260.96, found 260.61.

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 11398 - 11414.
[2]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00303.
[3]Patent: CN106831790,2017,A .Location in patent: Paragraph 0043-0046.
[4]Patent: WO2014/184069,2014,A1 .Location in patent: Page/Page column 33; 34.
[5]Patent: CN110194772,2019,A .Location in patent: Paragraph 0292; 0295; 0296; 0297.
[6]Canadian Journal of Chemistry,2018,vol. 96,p. 1093 - 1100.
[7]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.
[8]Patent: WO2017/161344,2017,A1 .Location in patent: Paragraph 0813; 0820.
[9]Journal of Medicinal Chemistry,2017,vol. 60,p. 9976 - 9989.
[10]Journal of Medicinal Chemistry,2019,vol. 62,p. 4158 - 4173.

2
[ 163622-50-2 ]
[ 1616484-34-4 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

3
[ 163622-50-2 ]
[ 1616484-36-6 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

4
[ 163622-50-2 ]
[ 1616484-42-4 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

5
[ 163622-50-2 ]
[ 1616484-44-6 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

6
[ 163622-50-2 ]
[ 1616484-22-0 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

7
[ 163622-50-2 ]
[ 1616484-30-0 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

8
[ 163622-50-2 ]
[ 1616484-38-8 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

9
[ 163622-50-2 ]
C₁₈H₂₅N₅O₂Si [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

10
[ 163622-50-2 ]
C₂₁H₂₂N₈O₂ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

11
[ 163622-50-2 ]
[ 1616484-24-2 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

12
[ 163622-50-2 ]
[ 1616484-26-4 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.

13
[ 163622-50-2 ]
[ 105-36-2 ]
[ 1616484-20-8 ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5158 - 5167.
[2]Canadian Journal of Chemistry,2018,vol. 96,p. 1093 - 1100.

14
[ 1615680-91-5 ]
[ 163622-50-2 ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E380-E383.

15
[ 123148-78-7 ]
[ 163622-50-2 ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E380-E383.

16
[ 163622-50-2 ]
N-cyclopropyl-3-ethynylbenzamide [ No CAS ]
3-[(4-amino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethynyl]-N-cyclopropylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 60℃; for 0.5h;Inert atmosphere; Microwave irradiation;	60 mg (0.245 mmol) of <strong>[163622-50-2]5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine</strong> (prepared as described in preparation 1) were dissolved in a microwave vial in 4 mL of dry DMF. 10 mg (0.048 mmol) of cupreous iodide, 48 mg (0.26 mmol) of N-cyclopropyl-3-ethynylbenzamide (prepared as described in preparation 8), 34 mg (0.048 mmol) of palladium dichloride bis(triphenylphosphine) and 346 muL of TEA were added to the reaction medium. The solvent was degassed under an argon stream for 10 minutes and the mixture submitted to microwave irradiation at 60C for 30 minutes and then filtered through a celite pad and evaporated to dryness. The residue was dissolved in DCM and washed with brine. The organic layer was dried over Na2S04 and evaporated. The crude was purified by flash-chromatography (DCM/MeOH 95/5) affording 23 mg (30%) of the title compound. 1H NMR (600 MHz, DMSO-d6) delta ppm 0.53 - 0.62 (m, 2 H) 0.68 - 0.74 (m, 2 H) 2.86 (tq, J=7.44, 3.89 Hz, 1 H) 2.82 - 2.90 (m, 1 H) 6.58 (br. s., 2 H) 7.44 - 7.53 (m, 1 H) 7.61 (s, 1 H) 7.70 (d, J=7.88 Hz, 1 H) 7.80 (d, J=7.88 Hz, 1 H) 7.98 (s, 1 H) 8.11 (s, 1 H) 8.52 (d, J=4.21 Hz, 1 H) 12.06 (br. s., 1 H) HRMS (ESI) calcd for C18H15N50 [M+H]+ 318.1350, found 318.1346.

References: [1]Patent: WO2014/184069,2014,A1 .Location in patent: Page/Page column 54.

17
[ 163622-50-2 ]
[ 74-88-4 ]
[ 862729-13-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; for 8.0h;	To a solution of 750 mg (2.88 mmol) of <strong>[163622-50-2]5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine</strong> in 20 mL of dry DMF, 190 muL (3.02 mmol) of methyl iodide and 795 mg (5.76 mmol) of anhydrous potassium carbonate were added. After 8 h the solvent was evaporated, the residue taken up with DCM and washed with water. The organic layer was dried over anhydrous Na2S04 and evaporated again to afford 394 mg (50%) of the title compound. HRMS (ESI) calcd for C7H7N4I [M+H]+ 274.9788, found 274.9788.

References: [1]Patent: WO2014/184069,2014,A1 .Location in patent: Page/Page column 34; 35.
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 11398 - 11414.

18
[ 163622-50-2 ]
N-(5-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-phenoxyphenyl)acrylamide [ No CAS ]