2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 58315450, compound

HRID 1483061Notes

Reaction equation

HRID 1483061 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[C:21]([O:25][C:26](=[O:40])[NH:27][CH:28]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[N:35][C:36]([NH2:39])=[CH:37][CH:38]=2)[CH2:29]1)([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26](=[O:40])[NH:27][CH:28]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[N:35][C:36]([NH:39][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([C:3](=[O:4])[N:2]([CH3:20])[CH3:1])[N:14]([CH:15]5[CH2:19][CH2:18][CH2:17][CH2:16]5)[C:8]=4[N:9]=3)=[CH:37][CH:38]=2)[CH2:29]1)([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 59290957HCID 59290957, compound

Product 1

HCID 58315450HCID 58315450, compoundYield 14.7%

Procedure

Using Buchwald Procedure A, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethyl amide (0.13 g, 0.444 mmol) and [1-(6-amino-pyridin-3-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (0.136 g, 0.488 mmol) gave {1-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (35 mg, 15%) (following SiO2 chromatography, eluting with 0-3% MeOH/dichloromethane).

Sources & evidence

ORD record
ord-4fa45098080c4bf6b338f113de307729
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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