4-(6-Aminopyridin-3-yl)-1,4-diazabicyclo[3.2.2]nonan-3-one → 7-cycloheptyl-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 627411Notes

Reaction equation

HRID 627411 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[N:8]([CH:16]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:7]=1.[NH2:23][C:24]1[N:29]=[CH:28][C:27]([N:30]2[CH:36]3[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]3)[CH2:32][C:31]2=[O:39])=[CH:26][CH:25]=1>>[CH:16]1([N:8]2[C:6]3[N:7]=[C:2]([NH:23][C:24]4[CH:25]=[CH:26][C:27]([N:30]5[CH:36]6[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]6)[CH2:32][C:31]5=[O:39])=[CH:28][N:29]=4)[N:3]=[CH:4][C:5]=3[CH:10]=[C:9]2[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 673544754-(6-Aminopyridin-3-yl)-1,4-diazabicyclo[3.2.2]nonan-3-oneHCID 866866262-chloro-7-cycloheptyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Product 1

HCID 673567137-cycloheptyl-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 77%

Procedure

Following general N—C coupling procedure 1, 2-chloro-7-cycloheptyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide was combined with 4-(6-aminopyridin-3-yl)-1,4-diazabicyclo[3.2.2]nonan-3-one and gave 7-cycloheptyl-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 (103 mg) in 77% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.73 (s, 1H), 8.66 (d, J=9.09 Hz, 1H), 8.17 (d, J=2.02 Hz, 1H), 8.14 (s, 1H), 7.55 (dd, J1=9.09 Hz, J2=2.53 Hz, 1H), 6.45 (s, 1H), 4.53 (m, 1H), 3.95 (s, 2H), 3.83 (m, 1H), 3.21 (m, 10H), 2.64 (m, 2H), 2.42 (m, 2H), 2.14-1.54 (m, 12H); HRMS m/z 517.3049 (M+H)+.

Sources & evidence

ORD record
ord-640c81e94a5e41a1b8177efd41bc5e3e
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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