3-Bromo-1,1,1-trifluoro-2-propanone → 1-(5-Bromo-4-(4-hydroxy-4-(trifluoromethyl)-4,5-dihydrothiazol-2-yl)pyridin-2-yl)-3-propylurea

HRID 2061860Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:15](=[S:17])[NH2:16])=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH3:14])=[O:10])=[N:6][CH:7]=1.Br[CH2:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22]>C(#N)C>[Br:1][C:2]1[C:3]([C:15]2[S:17][CH2:19][C:20]([OH:25])([C:21]([F:24])([F:23])[F:22])[N:16]=2)=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH3:14])=[O:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 5-bromo-2-(3-propylureido)pyridine-4-carbothioamide (Intermediate 44, 100 g, 315 mmol), 3-bromo-1,1,1-trifluoroacetone (64 mL, 630 mmol) in acetonitrile (1.5 L) was heated at 80° C. for 20 hours. The solution was then cooled down and was concentrated under reduced pressure. This gave an orange oil that was carried on without further purification.

Workup

temperatureThe solution was then cooled down
concentrationwas concentrated under reduced pressure
customThis gave an orange oil that
customwas carried on without further purification

Sources & evidence

ORD record: ord-9e339b77862749c1ba528b5858aec06c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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