Lithium Hydroxide → HCID 86656817, compound

HRID 410824Notes

Reaction equation

C[O:2][C:3](=[O:34])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:33]=[CH:32][C:12]2[N:13]([CH3:31])[C:14]([NH:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[N:15][C:11]=2[CH:10]=1)=[O:8].[Li+].[OH-]>>[F:30][C:27]([F:28])([F:29])[O:26][C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([NH:16][C:14]3[N:13]([CH3:31])[C:12]4[CH:32]=[CH:33][C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[O:8])=[CH:10][C:11]=4[N:15]=3)[S:18][C:19]=2[CH:25]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86656816HCID 86656816, compound

Product 1

HCID 86656817HCID 86656817, compoundYield 83.3%

Procedure

3-{[2-(6-Trifluoromethoxy-benzothiazol-2-ylamino)-1-methyl-1H-benzimidazole-5-carbonyl]-amino}-propionic acid (200 mg) was prepared by following General Procedure E starting from 3-{[2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1-methyl-1H-benz-imidazole-5-carbonyl]-amino}-propionic acid methyl ester (247 mg), and LiOH (1.0 ml, 2.0 N solution in water). LC/MS: m/z 481. 1H NMR (DMSO-d6, 400 MHz): δ 8.51 (t, 1H), 8.10 (br, 1H), 8.06 (s, 1H), 7.92 (s, 1H), 7.75 (d, 1H), 7.64 (br, 1H), 7.46 (d, 1H), 7.34 (d, 1H), 3.63 (s, 3H), 3.46 (m, 2H), and 2.58 (t, 2H), —COOH proton signal was not observed.

Sources & evidence

ORD record: ord-3564f0a7d5164a2d9c9cafc606bce67d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759535B2

Reaction notes

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