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]-piperidin-1-yl}-benzylidene)-thiazolidine-2,4-dione

HRID 1061241Notes

Reaction equation

HRID 1061241 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:21]=[CH:20][C:11]([CH:12]=[C:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:10][CH:9]=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:6]1[CH2:5][CH2:4][N:3]([C:8]2[CH:21]=[CH:20][C:11]([CH:12]=[C:13]3[S:17][C:16](=[O:18])[NH:15][C:14]3=[O:19])=[CH:10][CH:9]=2)[CH2:2][CH2:7]1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 738767195-[4-(Oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dione

Product 1

HCID 865845505-(4-{4-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzylidene)-thiazolidine-2,4-dione

Procedure

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-yl)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 36) 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 >240° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.45-1.60 (m, 2H), 2.00-2.15 (m, 2H), 2.86 (brt, J=9.0 Hz, 2H), 2.90-3.60 (m, 3H), 3.91 (brd, J=9.4 Hz, 1H), 3.93-4.10 (m, 3H), 5.40 (brs, 1H), 6.59 (d, J=6.0 Hz, 1H), 6.63 (d, J=6.0 Hz, 1H), 6.86 (t, J=6.0 Hz, 1H), 7.02 (d, J=6.6 Hz, 2H), 7.36 (s, 1H), 7.40 (d, J=6.6 Hz, 2H), 11.60 (s, 1H), 11.70 (brs, 1H); MS (ES) m/z: 509.9 (MH+); HRMS Calcd. for C25H28N5O5S(MH+): 510.1811. Found: 510.1861.

Sources & evidence

ORD record
ord-58ee9defc6c745c09eec613e471f89bb
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…