Trifluoroacetic acid → N-(3,4-dimethoxyphenyl)-2-(piperazin-1-yl)benzo[d]thiazole-6-carboxamide

HRID 447153Notes

Reaction equation

HRID 447153 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:35]=[CH:34][C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[S:20][C:16]=3[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:35]=[CH:34][C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[S:20][C:16]=3[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67235904Tert-butyl 4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate

Product 1

HCID 67236491N-(3,4-dimethoxyphenyl)-2-(piperazin-1-yl)benzo[d]thiazole-6-carboxamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate (507.1 mg, 1.15 mmol) was treated with trifluoroacetic acid (24 mL). The resulting homogenous mixture was stirred for 30 min, then diluted with diethyl ether and cooled in ice bath. The resulting solid was collected by filtration and dried in vacuum oven at room temperature to yield N-(3,4-dimethoxyphenyl)-2-(piperazin-1-yl)benzo[d]thiazole-6-carboxamide as a khaki colored amorphous solid.

Workup

  1. temperaturecooled in ice bath
  2. filtrationThe resulting solid was collected by filtration
  3. customdried in vacuum oven at room temperature

Sources & evidence

ORD record
ord-d7665c03f3b24f55906aad92aff5a9f9
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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