Acetic Anhydride → N-(6-(2-(ethyl(methyl)amino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)acetamide

HRID 1894755Notes

Reaction equation

[CH2:1]([N:3]([CH3:23])[CH:4]([CH2:21][CH3:22])[CH:5]([C:11]1[CH:20]=[CH:19][C:14]2[N:15]=[C:16]([NH2:18])[S:17][C:13]=2[CH:12]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)[CH3:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>C1COCC1>[CH2:1]([N:3]([CH3:23])[CH:4]([CH2:21][CH3:22])[CH:5]([C:11]1[CH:20]=[CH:19][C:14]2[N:15]=[C:16]([NH:18][C:24](=[O:26])[CH3:25])[S:17][C:13]=2[CH:12]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 6-(2-(ethyl(methyl)amino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine (50 mg, 0.151 mmol) and acetic anhydride (37 mg, 0.37 mmol) in THF (4 mL) was stirred at 40° C. over 3 days. The reaction was quenched with saturated sodium carbonate, extracted with 5% methanol in DCM. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative TLC to afford N-(6-(2-(ethyl(methyl)amino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)acetamide. MS ESI: m/z 372.28 [M+1+].

Workup

customThe reaction was quenched with saturated sodium carbonate
extractionextracted with 5% methanol in DCM
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by preparative TLC

Sources & evidence

ORD record: ord-15359178391649a49396c3bc13891cb8
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513291B2

Reaction notes

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