HCID 62916801, compound → HCID 118590304, compound
Reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1[C:31]1[CH:32]=[CH:33][C:34]2[N:35]([C:37]([C:40](O)=[O:41])=[CH:38][N:39]=2)[CH:36]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1[C:31]1[CH:32]=[CH:33][C:34]2[N:35]([C:37]([C:40]([NH:16][S:13]([C:10]3[CH:9]=[CH:8][C:7]([N:4]4[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]4)=[CH:12][CH:11]=3)(=[O:15])=[O:14])=[O:41])=[CH:38][N:39]=2)[CH:36]=1Participants
Procedure
The title compound was prepared by the method similar to that of Example 31 employing 4-(3-hydroxypyrrolidin-1-yl)benzene sulfonamide (Int-51) and 6-(2-(2,5-difluorophenyl)piperidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (Int 23) to afford an enantiomeric mixture which was purified by column chromatography using CHIRALPAK AD-H column and n-HEXANE:ETHANOL, 80:20 isocratic solution as eluent to afford 6-(2-(2,5-difluorophenyl)piperidin-1-yl)-N-((4-((S)-3-hydroxypyrrolidin-1-yl)phenyl)sulfonyl)imidazo[1,2-a]pyridine-3-carboxamide (0.012 g) (Isomer-II) MS (ESI): m/z 582.2 (M+H); 1H NMR (400 MHz, DMSO-d6) δ 12.00 (1H, S), 8.83 (1H, s), 8.4 (1H, s), 7.76-7.74 (2H, m), 7.58-7.56 (1H, m), 7.46-7.43 (1H, m), 7.07-6.99 (2H, m), 6.91-6.90 (1H, m), 6.65-6.62 (1H, m), 5.04-5.03 (1H, d), 4.42 (2H, bs), 3.50-3.38 (4H, m), 3.28-3.20 (1H, m), 2.90-2.85 (1H, m), 2.06-2.03 (1H, m), 1.91-1.88 (3H, m), 1.76-1.67 (1H, m), 1.64-1.53 (1H, m) ppm.
Workup
- customto afford an enantiomeric mixture which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-fa4651ceb8f646ca8f4fbf30e1917005
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394305B2
Reaction notes
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