Hydrochloric Acid → N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

HRID 1097450Notes

Reaction equation

HRID 1097450 reaction equation
[C:1]([C:3]1[C:11]2[S:10][C:9]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])=[N:8][C:7]=2[CH:6]=[CH:5][C:4]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25]C(=O)C(F)(F)F)[CH:20]=1)#[N:2].O.[OH-].[Li+].Cl>O1CCCC1.CO.O>[NH2:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][C:4]1[CH:5]=[CH:6][C:7]2[N:8]=[C:9]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[S:10][C:11]=2[C:3]=1[C:1]#[N:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86644684N-(7-cyano-6-{3-[(trifluoroacetyl)amino]phenoxy}-1,3-benzothiazol-2-yl)cyclopropanecarboxamide

Product 1

HCID 86644685N-[6-(3-aminophenoxy)-7-cyano-1,3-benzothiazol-2-yl]cyclopropanecarboxamideYield 95.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(7-Cyano-6-{3-[(trifluoroacetyl)amino]phenoxy}-1,3-benzothiazol-2-yl)cyclopropanecarboxamide (1.06 g, 2.37 mmol) was dissolved in a mixed solvent of tetrahydrofuran (25 mL)/methanol (25 mL)/water (25 mL), lithium hydroxide monohydrate (1.05 g, 25.7 mmol) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was neutralized with 1N hydrochloric acid, and concentrated under reduced pressure. The obtained residue was repeatedly washed with water to give the title compound (0.79 g, 95%) as a white powder.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. washThe obtained residue was repeatedly washed with water

Sources & evidence

ORD record
ord-58729610fa244ddba472ff3a99f2a5ea
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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