Triethylamine → [5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

HRID 1727353Notes

Reaction equation

Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([F:19])[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)=O.[NH2:20][C:21]([NH2:23])=[S:22].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[F:19][C:15]1[CH:14]=[C:13]([C:3]2[S:22][C:21]([NH2:23])=[N:20][C:4]=2[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=2)[CH:18]=[CH:17][N:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrobromide and thiourea (3.03 g, 39.8 mmol) in acetonitrile (50 mL) was added triethylamine (5.2 mL, 37.3 mmol), and the mixture was stirred for 2 hours at 80° C. Aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the deposited solid was collected by filtration. The resulted solid was washed with water, then, dried. The crude crystal was recrystallized from ethanol to obtain a title compound (3.67 g, yield 35%).

Workup

filtrationthe deposited solid was collected by filtration
washThe resulted solid was washed with water
customdried
customThe crude crystal was recrystallized from ethanol

Sources & evidence

ORD record: ord-28d15ba4273f46c4ae2df61e31aacb23
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495018B2

Reaction notes

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