4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 10301188, compound

HRID 1061246Notes

Reaction equation

HRID 1061246 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[CH:20][C:11]([CH2:12][CH:13]3[S:17][C:16](=[O:18])[NH:15][C:14]3=[O:19])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH:22][C@@H:23]([CH2:36][NH2:37])[CH2:24][O:25][C:26]1[C:34]2[NH:33][C:32](=[O:35])[NH:31][C:30]=2[CH:29]=[CH:28][CH:27]=1>>[OH:22][C@H:23]([CH2:24][O:25][C:26]1[C:34]2[NH:33][C:32](=[O:35])[NH:31][C:30]=2[CH:29]=[CH:28][CH:27]=1)[CH2:36][NH:37][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[CH:20][C:11]([CH2:12][CH:13]3[S:17][C:16](=[O:18])[NH:15][C:14]3=[O:19])=[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 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione

Product 1

HCID 10301188HCID 10301188, compound

Procedure

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) 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 73 as a pale yellowish solid; mp 173-175° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.45-1.60 (m, 2H), 1.90-2.15 (m, 2H), 2.10-2.95 (m, 5H), 3.03 (brd, J=10.5 Hz, 1H), 3.26 (dd, J=14.1, 3.8 Hz, 1H), 3.68 (brd, J=12.4 Hz, 2H), 3.95-4.05 (m, 3H), 4.51 (dd, J=10.0, 4.0 Hz, 1H), 6.58 (d, J=7.8 Hz, 1H), 6.63 (d, J=8.1 Hz, 1H), 6.75-6.95 (m, 3H), 7.05 (d, J=8.7 Hz, 2H), 11.60 (s, 1H), 11.85 (brs, 1H); MS (ES) m/z: 512.0 (MH+); HRMS Calcd. for C25H30N5O5S (MH+): 512.1968. Found: 512.1982.

Sources & evidence

ORD record
ord-9dfb61886a2640f08b88758054557b2c
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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