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

HRID 455168Notes

Reaction equation

HRID 455168 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-b8aac04455a14e799a3fd0be920b040d
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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