4-Fluoro-1,3-benzothiazol-2-amine → HCID 86584917, compound

HRID 2250701Notes

Reaction equation

HRID 2250701 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:5]=2[N:6]=1.[CH3:12][C:13]1[S:17][C:16]([C:18](Cl)=[O:19])=[CH:15][CH:14]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:11][C:7]1[C:5]2[N:6]=[C:2]([NH:1][C:18]([C:16]3[S:17][C:13]([CH3:12])=[CH:14][CH:15]=3)=[O:19])[S:3][C:4]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 20498874-Fluoro-1,3-benzothiazol-2-amineHCID 27600835-Methylthiophene-2-carbonyl chloride

Product 1

HCID 86584917HCID 86584917, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

2-Amino-4-flourobenzothiazol (84 mg, 0.50 mmol) is dissolved in pyridine (3 ml) and treated with 4-dimethylaminopyridine (1 mg) and 5-methyl-thiophene-2-carbonyl chloride (161 mg, 1.0 mmol). After stirring for 1 h at ambient temperature, the reaction mixture was evaporated to dryness. Flash chromatography on silica (eluent diethyl ether/cyclohexane 1:1 containing 0.5% of 25% aqueous ammonia) and final recrystallization from ethyl acetate affords the product as off-white solid. (34 mg, 69%). MS: m/e=292 (M+).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customFlash chromatography on silica (eluent diethyl ether/cyclohexane 1:1 containing 0.5% of 25% aqueous ammonia) and final recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-19393b0ade364950aa7dedac592274e4
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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