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

HRID 2300239Notes

Reaction equation

HRID 2300239 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1.[OH:25][C@@H:26]([CH2:39][NH2:40])[CH2:27][O:28][C:29]1[C:37]2[NH:36][C:35](=[O:38])[NH:34][C:33]=2[CH:32]=[CH:31][CH:30]=1>>[OH:25][C@H:26]([CH2:27][O:28][C:29]1[C:37]2[NH:36][C:35](=[O:38])[NH:34][C:33]=2[CH:32]=[CH:31][CH:30]=1)[CH2:39][NH:40][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:23][CH:24]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 187677925-[4-(4-Oxo-piperidine-1-sulfonyl)-benzyl]-thiazolidine-2,4-dione

Product 1

HCID 102317815-(4-{4-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidine-1-sulfonyl}-benzyl)-thiazolidine-2,4-dione

Procedure

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-sulfonyl)-benzyl]-thiazolidine-2,4-dione and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one according to the reductive amination procedure of Intermediate 21 as a pale grey solid; 1H NMR (300 MHz, DMSO-d6): δ 1.20-1.40 (m, 2 H), 1.80-2.00 (m, 2 H), 2.30-4.00 (m, 12 H), 4.65 (dd, J=8.0, 3.5 Hz, 1 H), 6.56 (d, J=3.2 Hz, 1 H), 6.59 (d, J=3.8 Hz, 1 H), 6.85 (t, J=3.5 Hz, 1 H), 7.50 (d, J=8.1 Hz, 2 H), 7.66 (d, J=8.1 Hz, 2 H), 10.70 (s, 1 H), 10.79 (brs, 1 H); MS (ES) m/z : 576.0 (M++H); HRMS Calcd. for C25H30N507S2 (M++H): 576.1587. Found: 576.1596.

Sources & evidence

ORD record
ord-c40a6b6d12a04a558d4c63708d9d831f
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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