2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 53377719, compound

HRID 627418Notes

Reaction equation

HRID 627418 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[O:10][C:9]2=[O:19])=[CH:4][CH:3]=1.[CH3:20][N:21]([CH3:39])[C:22]([C:24]1[N:33]([CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:27]2[N:28]=[C:29](Cl)[N:30]=[CH:31][C:26]=2[CH:25]=1)=[O:23]>>[CH:34]1([N:33]2[C:27]3[N:28]=[C:29]([NH:1][C:2]4[CH:3]=[CH:4][C:5]([N:8]5[CH2:12][C:11]6([CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]6)[O:10][C:9]5=[O:19])=[CH:6][N:7]=4)[N:30]=[CH:31][C:26]=3[CH:25]=[C:24]2[C:22]([N:21]([CH3:39])[CH3:20])=[O:23])[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

3

Reactant 2

HCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 67356262HCID 67356262, compound

Product 1

HCID 53377719HCID 53377719, compoundYield 50.4%

Procedure

Following general N—C coupling procedure 1, 3-(6-Amino-pyridin-3-yl)-1-oxa-3,8-diaza-spiro[4.6]undecan-2-one (0.100 g, 0.276 mmol) was combined with 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (0.081 g, 0.276 mmol, 1.0 eq) which gave 7-cyclopentyl-N,N-dimethyl-2-(5-(2-oxo-1-oxa-3,8-diazaspiro[4.6]undecan-3-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide as white solid (0.075 g, 0.139 mmol) in 50% yield. 1H NMR (400 MHz, CDCl3) 6 ppm 1.58-1.82 (m, 4H) 1.97-2.27 (m, 14H) 2.47-2.65 (m, 2H) 2.86-3.11 (m, 4H) 3.16 (s, 7H) 3.80-3.88 (m, 2H) 4.80 (qd, J=8.95, 8.78 Hz, 1H) 6.46 (s, 1H) 8.06 (s, 1H) 8.13 (dd, J=9.03, 3.01 Hz, 1H) 8.21-8.32 (m, 1H) 8.50 (d, J=9.03 Hz, 1H) 8.72 (s, 1H); HRMS calc for m/z=531.2832 and found m/z=531.2858 (M+H)+.

Sources & evidence

ORD record
ord-53be1dc8e88f43258572d1769dd41796
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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