Lithium Hydroxide → HCID 58397443, compound

HRID 410794Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 58397453HCID 58397453, compound

Product 1

HCID 58397443HCID 58397443, compoundYield 60%

Procedure

6-Diethylamino-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (175 mg) was prepared by following General Procedure E starting from 6-diethylamino-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester (300 mg) and lithium hydroxide (102 mg). LC/MS: m/z 480.9. 1H NMR (DMSO-d6, 400 MHz): δ 12.45 (bs, 1H), 8.25 (bs, 1H), 7.96 (s, 1H), 7.85 (s, 1H), 7.80-7.62 (m, 1H), 7.38 (d, 1H), 3.68 (s, 3H), 3.41-3.25 (m, 4H), 0.94 (t, 6H), —COOH proton signal was not observed.

Sources & evidence

ORD record: ord-b48bb071cfab4ea6a0657f8b49a6473a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759535B2

Reaction notes

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