4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 69655006, compound

HRID 1061377Notes

Reaction equation

HRID 1061377 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C:13](=[O:14])[N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]5)=[CH:27][CH:26]=4)(=[O:23])=[O:22])=[CH:17][CH:16]=3)[N:11]=[N:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:38][C@@H:39]([CH2:52][NH2:53])[CH2:40][O:41][C:42]1[C:50]2[NH:49][C:48](=[O:51])[NH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1>>[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C:13](=[O:14])[N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH2:32][CH2:33][CH:34]([NH:53][CH2:52][C@H:39]([OH:38])[CH2:40][O:41][C:42]6[C:50]7[NH:49][C:48](=[O:51])[NH:47][C:46]=7[CH:45]=[CH:44][CH:43]=6)[CH2:35][CH2:36]5)=[CH:27][CH:26]=4)(=[O:23])=[O:22])=[CH:17][CH:16]=3)[N:11]=[N:10]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 22220255HCID 22220255, compound

Product 1

HCID 69655006HCID 69655006, compound

Procedure

The title compound was prepared from 4-[4-(3-cyclopentyl-propyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 226) 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 0.90-4.00 (m, 29H), 5.10-5.30 (m, 1H), 6.58 (d, J=7.9 Hz, 1H), 6.61 (d, J=7.9 Hz, 1H), 6.81 (d, J=8.9 Hz, 2H), 6.89 (d, J=8.9 Hz, 2H), 6.90 (dd, J=7.9, 7.9 Hz, 1H), 7.86 (d, J=8.5 Hz, 2H), 8.07 (d, J=8.5 Hz, 2H), 10.70 (s, 1H), 10.80 (s, 1H); MS (ES) m/z: 732.3 (MH+); HRMS Calcd. for C36H46N9O6S(MH+): 732.3292. Found: 732.3294.

Sources & evidence

ORD record
ord-33e1b1fc314e40ecbc1cd17bcb24dfd2
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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