4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 145832531, compound

HRID 1794755Notes

Reaction equation

HRID 1794755 reaction equation
[NH:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[S: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]([CH2:36][NH:37][CH:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:8][CH:4]3[S:3][C:2](=[NH:1])[NH:6][C:5]3=[O:7])=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)[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

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 145832527HCID 145832527, compound

Product 1

HCID 145832531HCID 145832531, compound

Procedure

The title compound: was prepared from 1-[4-(2-imino-4-oxo-thiazolidin-5-ylmethyl)-phenyl]-piperidin-4-one (which was obtained in Example 45) 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>155° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.40 (m, 2 H), 1.80–1.95 (m, 2 H), 2.50–2.90 (m, 6 H), 3.24 (dd, J=14.1, 4.0 Hz; 1 H), 3.50–3.75 (m, 2 H), 3.80–4.05 (m, 3 H), 4.50 (dd, J=9.8, 4.0 Hz, 1 H), 4.88 (brs, 1 H), 6.57 (d, J=7.8 Hz, 1 H), 6.62 (d, J=8.1 Hz, 1 H), 6.80–6.90 (m, 3 H), 7.04 (d, J=8.7 Hz, 2 H), 8.73 (brs, 1 H); MS (ES) m/z: 256.3 ((M+2H)2+, 100%), 511.2 (MH+, 10%); HRMS Calcd. for C25H31N6O4S (MH+): 511.2128. Found: 511.2122.

Sources & evidence

ORD record
ord-cb2b6861c6d64c0091c2ad6eecc102b9
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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