4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → 5-(3-Fluoro-4-{4-[(2S)-2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

HRID 1061234Notes

Reaction equation

HRID 1061234 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:16])[CH2:4][O:5][C:6]1[C:14]2[NH:13][C:12](=[O:15])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[F:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)[CH2:21][CH:22]1[S:26][C:25](=[O:27])[NH:24][C:23]1=[O:28]>>[F:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][CH:35]([NH:1][CH2:2][C@H:3]([OH:16])[CH2:4][O:5][C:6]2[C:14]3[NH:13][C:12](=[O:15])[NH:11][C:10]=3[CH:9]=[CH:8][CH:7]=2)[CH2:34][CH2:33]1)[CH2:21][CH:22]1[S:26][C:25](=[O:27])[NH:24][C:23]1=[O:28]

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 222205525-[3-Fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione

Product 1

HCID 101431415-(3-Fluoro-4-{4-[(2S)-2-hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

Procedure

The title compound was prepared from 4-((2S)-3-amino-2-hydroxy-propoxy)-1,3-dihydro-benzoimidazol-2-one (U.S. Pat. No. 5,786,356/1998) and 5-[3-fluoro-4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 61) according to the procedure of Example 63 as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.56-1.62 (m, 2H), 2.04 (m, 2H), 2.63-2.75 (m, 5H), 2.86-2.95 (m, 4H), 3.01-3.10 (m, 4H), 4.50-4.55 (m, 1H), 5.33 (brs, 1H), 6.57-6.65 (m, 2H), 6.84-7.09 (m, 3H), 8.22 (s, 1H), 7.22-7.29 (m, 1H), 10.55 (s, 1H), 10.65 (s, 1H); MS (ES) m/z: 530.0 (MH+); HRMS Calcd. for C25H29FN5O5S(MH+): 530.1873. Found: 530.1876.

Sources & evidence

ORD record
ord-592621172a9e41b3b84a5fcb6c5b5489
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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