Hydrochloric Acid → N-(3,4-dimethoxyphenyl)-2-(2-(methylamino)ethylamino)benzo[d]thiazole-6-carboxamide

HRID 447149Notes

Reaction equation

HRID 447149 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:34]=[CH:33][C:17]3[N:18]=[C:19]([NH:21][CH2:22][CH2:23][N:24](C)[C:25](=O)OC(C)(C)C)[S:20][C:16]=3[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:34]=[CH:33][C:17]3[N:18]=[C:19]([NH:21][CH2:22][CH2:23][NH:24][CH3:25])[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 313Hydrochloric AcidHCID 86654768Tert-butyl 2-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-ylamino)ethyl(methyl)carbamate

Product 1

HCID 86654769N-(3,4-dimethoxyphenyl)-2-(2-(methylamino)ethylamino)benzo[d]thiazole-6-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 2-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-ylamino)ethyl(methyl)carbamate (327.1 mg, 0.672 mmol) was dissolved in 1,4-dioxane (4 mL) and then treated with 4N HCl in 1,4-dioxane (4 mL, 16.0 mmol). The resulting mixture was stirred for 2 h and a solid separated from the solution. The solid was collected by filtration, washed with 1,4-dioxane, then dried in vacuum oven for 2 d at room temperature to yield the hydrochloride salt of N-(3,4-dimethoxyphenyl)-2-(2-(methylamino)ethylamino)benzo[d]thiazole-6-carboxamide as a yellow solid.

Workup

  1. customa solid separated from the solution
  2. filtrationThe solid was collected by filtration
  3. washwashed with 1,4-dioxane
  4. customdried in vacuum oven for 2 d at room temperature

Sources & evidence

ORD record
ord-7d509f944eb8421d80da0f8e8e1ebf83
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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