4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 69654824, compound

HRID 1061374Notes

Reaction equation

HRID 1061374 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH:28][C@@H:29]([CH2:42][NH2:43])[CH2:30][O:31][C:32]1[C:40]2[NH:39][C:38](=[O:41])[NH:37][C:36]=2[CH:35]=[CH:34][CH:33]=1>>[OH:28][C@H:29]([CH2:30][O:31][C:32]1[C:40]2[NH:39][C:38](=[O:41])[NH:37][C:36]=2[CH:35]=[CH:34][CH:33]=1)[CH2:42][NH:43][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 69654824HCID 69654824, compound

Procedure

The title compound was prepared from N-{4-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one (U.S. Pat. No. 5,786,356/1998) according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.60-1.80 (m, 2H), 2.00-2.15 (m, 2H), 2.06 (s, 3H), 2.50-2.70 (m, 2H), 2.90-3.20 (m, 3H), 3.60-3.75 (m, 2H), 4.15-4.25 (m, 1H), 5.70 (brs, 1H), 6.61 (t, J=8.7 Hz, 1H), 6.80-6.92 (m, 5H), 7.60 (d, J=9.0 Hz, 2H), 7.70 (d, J=9.0 Hz, 2H), 9.72 (brs, 1H), 10.42 (s, 1H), 10.65 (s, 1H), 10.80 (s, 1); MS (ES) m/z: 595.2 (MH+); HRMS Calcd. for C29H35N6O6S(MH+): 595.2339. Found: 595.2332.

Sources & evidence

ORD record
ord-061c48d1821d47118dfd1c033f2026b8
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…