2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 67355893, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][CH2:24][C@@:11]2([O:15][C:14](=[O:16])[N:13]([C:17]3[CH:18]=[N:19][C:20]([NH2:23])=[CH:21][CH:22]=3)[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28]([CH3:46])[C:29]([C:31]1[N:40]([CH:41]2[CH2:45][CH2:44][CH2:43][CH2:42]2)[C:34]2[N:35]=[C:36](Cl)[N:37]=[CH:38][C:33]=2[CH:32]=1)=[O:30]>>[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][CH2:24][C@@:11]2([O:15][C:14](=[O:16])[N:13]([C:17]3[CH:18]=[N:19][C:20]([NH:23][C:36]4[N:37]=[CH:38][C:33]5[CH:32]=[C:31]([C:29](=[O:30])[N:28]([CH3:27])[CH3:46])[N:40]([CH:41]6[CH2:45][CH2:44][CH2:43][CH2:42]6)[C:34]=5[N:35]=4)=[CH:21][CH:22]=3)[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
Following general N—C coupling procedure 1, (R)-3-(6-Amino-pyridin-3-yl)-2-oxo-1-oxa-3,8-diaza-spiro[4.6]undecane-8-carboxylic acid tert-butyl ester was combined with 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide which gave (R)-3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-2-oxo-1-oxa-3,8-diaza-spiro[4.6]undecane-8-carboxylic acid tert-butyl ester as a white solid (0.175 g, 0.272 mmol) in 66% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (s, 9H) 1.61-1.78 (m, 3H) 1.79-1.96 (m, 3H) 1.96-2.14 (m, 7H) 2.38-2.48 (m, 2H) 3.06 (d, J=10.54 Hz, 6H) 3.20-3.33 (m, 2H) 3.36-3.63 (m, 2H) 3.82-3.97 (m, 2H) 4.75 (quin, J=8.78 Hz, 1H) 6.63 (5, 1H) 7.98 (d, J=9.03 Hz, 1H) 8.34 (d, J=9.54 Hz, 1H) 8.44 (s, 1H) 8.81 (s, 1H) 9.78 (s, 1H). MS m/z 619.5 (M+H)+.
Sources & evidence
- ORD record
- ord-79691f1913b94412921c6b82a2386c51
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957074B2
Reaction notes
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