Pyrrolidine → HCID 178457822, compound
Reaction equation
[CH:1]([NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:21]3[CH:20]=[C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[N:18]=[CH:17][C:16]=3[NH:15]/[C:14]/2=[N:31]\[C:32]([N:34]2[CH2:39][CH2:38]O[CH2:36][CH2:35]2)=[O:33])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].N1CCCC1>>[CH:1]([NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:21]3[CH:20]=[C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[N:18]=[CH:17][C:16]=3[NH:15]/[C:14]/2=[N:31]\[C:32]([N:34]2[CH2:35][CH2:36][CH2:38][CH2:39]2)=[O:33])[CH2:9][CH2:8]1)=[O:6])([CH3:2])[CH3:3]Participants
3
Procedure
The title compound was synthesized using a method analogous to the preparation of (E)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)morpholine-4-carboxamide, using pyrrolidine as the amine source (4.5% yield). MS m/z=526.5 [M+H], calc 525.69 for C28H43N7O3. 1H NMR (DMSO-d6) δ ppm: 11.77 (s., 1H), 7.98 (s, 1H), 7.62 (d, J=1.0 Hz, 1H), 6.79 (s, 1H), 4.45-4.58 (m, 1H), 4.30 (t, J=1.0 Hz, 2H), 3.85-4.00 (m, 1H), 3.43-3.53 (m, 2H), 3.30-3.36 (m, 2H), 2.61 (t, J=1.0 Hz, 2H), 2.52-2.59 (m, 2H), 2.36-2.47 (m, 5H), 2.01-2.10 (m, 2H), 1.75-1.86 (m, 4H), 1.53-1.65 (m, 2H), 1.43-1.53 (m, 6H), 1.32-1.42 (m, 2H), 1.08 (d, J=6.6 Hz, 6H).
Sources & evidence
- ORD record
- ord-1fef6217037a4657a6e28dbbad00f625
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115127B2
Reaction notes
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