4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → Methyl[4-({4-[4-({(2s)-2-hydroxy-3-[(2-oxo-2,3-dihydro-1h-benzimidazol-4-yl)oxy]propyl}amino)-1-piperidineyl]anilino}sulfonyl)phenoxy]acetate

HRID 1061398Notes

Reaction equation

HRID 1061398 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:28])(=[O:27])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[OH:30][C@@H:31]([CH2:44][NH2:45])[CH2:32][O:33][C:34]1[C:42]2[NH:41][C:40](=[O:43])[NH:39][C:38]=2[CH:37]=[CH:36][CH:35]=1>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([NH:45][CH2:44][C@H:31]([OH:30])[CH2:32][O:33][C:34]4[C:42]5[NH:41][C:40](=[O:43])[NH:39][C:38]=5[CH:37]=[CH:36][CH:35]=4)[CH2:22][CH2:21]3)=[CH:18][CH:19]=2)(=[O:28])=[O:27])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 69654907{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenoxy}-acetic acid methyl ester

Product 1

HCID 91369965Methyl[4-({4-[4-({(2s)-2-hydroxy-3-[(2-oxo-2,3-dihydro-1h-benzimidazol-4-yl)oxy]propyl}amino)-1-piperidineyl]anilino}sulfonyl)phenoxy]acetate

Procedure

The title compound was prepared from {4-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenoxy}-acetic acid methyl ester (which was obtained in Example 232) 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 278 as a pale yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.75-1.90 (m, 2H), 2.50-2.85 (m, 5H), 3.30-3.50 (m, 2H), 3.69 (s, 3H), 3.80-4.05 (m, 3H), 4.87 (s, 2H), 6.56 (d, J=7.8 Hz, 1H), 6.61 (d, J=8.1 Hz, 1H), 6.65-6.90 (m, 5H), 7.02 (d, J=9.0 Hz, 2H), 7.59 (d, J=9.0 Hz, 2H), 10.60 (s, 1H), 10.75 (brs, 1H); MS (ES) m/z: 626.1 (MH+); HRMS Calcd. for C30H36N5O8S(MH+): 626.2285. Found: 626.2298.

Sources & evidence

ORD record
ord-e64a4e9f2a384785a6c171b5a9b90437
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…