4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 178518146, compound
Reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][C:12](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[C:13](=[O:15])[N:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]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>>[OH:30][C@@H:31]([CH2:44][NH:45][CH:26]1[CH2:25][CH2:24][N:23]([C:20]2[CH:19]=[CH:18][C:17]([CH:16]=[C:12]3[S:11][C:10]([NH:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[N:14][C:13]3=[O:15])=[CH:22][CH:21]=2)[CH2:28][CH2:27]1)[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]=1Participants
Procedure
The title compound was prepared from 1-{4-[2-(2-morpholin-4-ylethylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-phenyl}-piperidin-4-one(which was obtained in Intermediate 20) and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one (Jesudason, C. D., et al., EP 0 764 640) according to the procedure of Example 1 as a pale yellowish solid; mp>140° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.45 (m, 2 H), 1.75-2.00 (m, 2 H), 2.43 (t, J=4.7 Hz, 2 H), 2.50-3.70 (m, 13H), 3.59 (t, J=4.7 Hz, 2 H), 3.75-4.15 (m, 5H), 4.86 (brs, 1 H), 6.57 (d, J=7.5 Hz, 1 H), 6.62 (d, J=7.5 Hz, 1 H), 6.87 (t, J=8.1 Hz, 1 H), 7.02 (d, J=9.0 Hz, 2 H), 7.38 (d, J=9.0 Hz, 2 H), 7.47 (s, 1 H), 9.47 (s, 1 H), 10.57 (s, 1 H), 10.70 (brs, 1 H); MS (ES) m/z: 311.5 ((M+2H)2+, 100%); 621.9 (MH+, 15%); HRMS Calcd. for C31H40N7O5S (MH+): 622.2812. Found: 622.2811.
Sources & evidence
- ORD record
- ord-51f3f8415675407581e99c796d4c8392
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06583140B2
Reaction notes
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