2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 58315429, compound

HRID 1853186Notes

Reaction equation

HRID 1853186 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[C:11](=[O:16])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:36])[C:19]([C:21]1[N:30]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:24]2[N:25]=[C:26](Cl)[N:27]=[CH:28][C:23]=2[CH:22]=1)=[O:20]>>[CH3:17][N:18]([CH3:36])[C:19]([C:21]1[N:30]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:24]2[N:25]=[C:26]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][N:9]4[CH2:14][CH2:13][N:12]([CH3:15])[C:11](=[O:16])[CH2:10]4)=[CH:6][N:7]=3)[N:27]=[CH:28][C:23]=2[CH:22]=1)=[O:20]

Participants

3

Reactant 2

HCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 58315461HCID 58315461, compound

Product 1

HCID 58315429HCID 58315429, compoundYield 20.4%

Procedure

Following Buchwald method B, 4-(6-amino-pyridin-3-ylmethyl)-1-methyl-piperazin-2-one (30 mg, 0.136 mmol) and 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (33 mg, 0.113 mmol) give 7-cyclopentyl-2-[5-(4-methyl-3-oxo-piperazin-1-ylmethyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (11 mg, 21%) [following SiO2 chromatography eluting with 1-10% (2M NH3 in MeOH)/DCM]

Sources & evidence

ORD record
ord-9e002da7e69d4e798b2af635c1f607b8
Source dataset
uspto-grants-2015_02
Patent number
US08962630B2

Reaction notes

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