2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 67375795, compound

HRID 1850646Notes

Reaction equation

HRID 1850646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][N:11]([C:18]1[CH:19]=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[C:12](=[O:17])[CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:26]1[N:27]=[CH:28][C:29]2[CH:34]=[C:33]([C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[N:32]([CH:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[C:30]=2[N:31]=1>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][N:11]([C:18]1[CH:19]=[N:20][C:21]([NH:24][C:26]3[N:27]=[CH:28][C:29]4[CH:34]=[C:33]([C:35](=[O:36])[N:37]([CH3:38])[CH3:39])[N:32]([CH:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[C:30]=4[N:31]=3)=[CH:22][CH:23]=1)[C:12](=[O:17])[CH2:13]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 67354835HCID 67354835, compound

Product 1

HCID 67375795HCID 67375795, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent2×

Procedure

Following general Scheme 5 on a 1.023 mmole scale, 3-(6-Amino-pyridin-3-yl)-4-oxo-3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester was combined with 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide which yielded after SiO2 gel Chromatograped (5-8% CH3OH-ethyl acetate), 0.57 grams (95% yield) of 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-4-oxo-3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester, TLC RF 0.4 in 5% CH3OH-ethyl acetate, MS m/z 589 (M+H)+

Sources & evidence

ORD record
ord-0036690211754f7db0c131280b2f6bd6
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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