Lithium Hydroxide → 4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamoyl)benzoic acid

HRID 538878Notes

Reaction equation

[CH3:1][N:2]([CH3:34])[CH:3]([CH2:32][CH3:33])[CH:4]([C:10]1[CH:31]=[CH:30][C:13]2[N:14]=[C:15]([NH:17][C:18]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=3)=[O:19])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][N:2]([CH3:34])[CH:3]([CH2:32][CH3:33])[CH:4]([C:10]1[CH:31]=[CH:30][C:13]2[N:14]=[C:15]([NH:17][C:18]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)=[O:19])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamoyl)benzoate (15 mg, 0.031 mmol) and lithium hydroxide (6.6 mg, 0.157 mmol) in dioxane (2 mL) and water (1 mL) was stirred at 50° C. for 4 h. The reaction was evaporated, water was added and neutralized to pH 7. The slurry obtained was evaporated and extracted with DCM-methanol mixture and evaporated. The crude acid was purified by PTLC using DCM-methanol mixture as eluent to afford 4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamoyl)benzoic acid. MS ESI: m/462.11 [M−1−].

Workup

customThe reaction was evaporated
additionwater was added
customThe slurry obtained
customwas evaporated
extractionextracted with DCM-methanol mixture
customevaporated
customThe crude acid was purified by PTLC

Sources & evidence

ORD record: ord-226ba5a41943413097a543009669f4af
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865752B2

Reaction notes

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