1-Methylcyclopropane-1-sulfonamide → HCID 118590548, compound

HRID 1054478Notes

Reaction equation

HRID 1054478 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([C:27](O)=[O:28])=[CH:25][N:26]=3)[CH:23]=2)[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[CH3:30][C:31]1([S:34]([NH2:37])(=[O:36])=[O:35])[CH2:33][CH2:32]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([C:27]([NH:37][S:34]([C:31]4([CH3:30])[CH2:33][CH2:32]4)(=[O:36])=[O:35])=[O:28])=[CH:25][N:26]=3)[CH:23]=2)[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Participants

3

Reactant 2

HCID 218898141-Methylcyclopropane-1-sulfonamideHCID 118590436HCID 118590436, compound

Product 1

HCID 118590548HCID 118590548, compound

Procedure

The title compound was prepared by the method similar to that of Example 31 employing 6-(2-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (Int 42) and 1-Methylcyclopropane-1-sulfonamide (int-50) to afford an enantiomeric mixture, which was purified by chiral chromatography employing CHIRALPAK AD-H column with n-HEXANE:ETHANOL, 60:40 Isocratic solution as eluent. MS (ESI): m/z 515.2 (M+H); 1H NMR (600 MHz, DMSO-d6) δ 11.88 (1H, s), 8.74 (1H, s), 8.55 (1H, s), 7.65-7.64 (1H, d, J=10.4 Hz), 7.52-7.50 (1H, d, J=10.4 Hz), 6.51-6.45 (2H, m), 4.45-4.42 (3H, m), 4.30-4.22 (2H, m), 3.64-3.62 (1H, d), 2.79-2.73 (1H, m), 1.90-1.78 (4H, m), 1.57-1.53 (8H, m), 1.23-1.03 (2H, m) ppm.

Workup

  1. customto afford an enantiomeric mixture, which
  2. customwas purified by chiral chromatography

Sources & evidence

ORD record
ord-4c6215ad00394b2fb414026d69af82e8
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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