2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → 7-cyclopentyl-N,N-dimethyl-2-(5-(3-oxo-1,4-diazabicyclo[3.2.2]nonan-4-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

HRID 627410Notes

Reaction equation

HRID 627410 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10][C:9]2=[O:17])=[CH:4][CH:3]=1.Cl[C:19]1[N:20]=[CH:21][C:22]2[CH:27]=[C:26]([C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[N:25]([CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[C:23]=2[N:24]=1>>[CH:33]1([N:25]2[C:23]3[N:24]=[C:19]([NH:1][C:2]4[CH:3]=[CH:4][C:5]([N:8]5[CH:14]6[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]6)[CH2:10][C:9]5=[O:17])=[CH:6][N:7]=4)[N:20]=[CH:21][C:22]=3[CH:27]=[C:26]2[C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

3

Reactant 2

HCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 673544754-(6-Aminopyridin-3-yl)-1,4-diazabicyclo[3.2.2]nonan-3-one

Product 1

HCID 533778377-cyclopentyl-N,N-dimethyl-2-(5-(3-oxo-1,4-diazabicyclo[3.2.2]nonan-4-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideYield 86%

Procedure

Following general N—C coupling procedure 1, 4-(6-aminopyridin-3-yl)-1,4-diazabicyclo[3.2.2]nonan-3-one was combined with 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide and gave 7-cyclopentyl-N,N-dimethyl-2-(5-(3-oxo-1,4-diazabicyclo[3.2.2]nonan-4-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, 99 mg in 86% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (s, 1H), 8.55 (d, J=9.09 Hz, 1H), 8.16 (d, J=2.02 Hz, 1H), 8.09 (s, 1H), 7.55 (dd, J1=9.09 Hz, J2=2.53 Hz, 1H), 6.47 (s, 1H), 4.81 (m, 1H), 3.93 (s, 2H), 3.82 (m, 1H), 3.19 (m, 10H), 2.59 (m, 2H), 2.41 (m, 2H), 2.07 (m, 6H), 1.74 (m, 2H); HRMS m/z 489.2740 (M+H)+.

Sources & evidence

ORD record
ord-77eba73ec75e4dce886fb9933ff1971d
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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