4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 10303498, compound

HRID 1278762Notes

Reaction equation

[CH3:1][NH:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:28][CH2:27][C:22]3(OCCO3)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[O:4].[NH2:29][CH2:30][C@H:31]([OH:44])[CH2:32][O:33][C:34]1[C:42]2[NH:41][C:40](=[O:43])[NH:39][C:38]=2[CH:37]=[CH:36][CH:35]=1>>[CH3:1][NH:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:28][CH2:27][CH:22]([NH:29][CH2:30][C@H:31]([OH:44])[CH2:32][O:33][C:34]3[C:42]4[NH:41][C:40](=[O:43])[NH:39][C:38]=4[CH:37]=[CH:36][CH:35]=3)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[O:4]

Participants

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one

HCID 69900398HCID 69900398, compound

Product 1

HCID 10303498HCID 10303498, compound

Procedure

Reference Example 20, 1-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzenesulfonyl]-pyrrolidine-2-carboxylic acid methylamide, was hydrolyzed to the corresponding ketone according to the procedure of Reference Example 5, and then reacted with 4-((2S)-3-amino-2-hydroxy-propoxy)-1,3-dihydro-benzoimidazol-2-one according to the procedure of Example 1 to give the title compound as a tan solid; mp 36-39° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.20-2.00 (m, 8H), 2.55 (d, 3H), 2.50-3.40 (m, 6H), 3.70-4.10 (m, 6H), 4.85-4.95 (m, 1H), 6.55 (d, 1H), 6.60 (d, 1H), 6.80 (t, 2H), 7.35 (d, 2H), 7.60 (d, 2H), 7.90 (q, 1H), 10.60 (br s, 1H), 10.70 (br s, 1H), MS (ES) m/z: 573.1 (MH+); HRMS Calcd. for C27H37N6O6S (MH+): 573.2490. Found: 573.2495.

Sources & evidence

ORD record: ord-20567c8eb79948f8977a38a2de98499b
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444685B1

Reaction notes

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