Chloroacetone → HCID 24826754, compound

HRID 911014Notes

Reaction equation

HRID 911014 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[Br:6][C:7]1[C:8]([O:17][C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=2[F:25])=[CH:9][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[N:11][CH:12]=1.C(N(CC)CC)C>C(O)C>[Br:6][C:7]1[C:8]([O:17][C:18]2[C:19]([F:25])=[CH:20][CH:21]=[CH:22][C:23]=2[F:24])=[CH:9][C:10]([NH:13][C:14]2[S:15][CH:2]=[C:3]([CH3:4])[N:16]=2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 86634746HCID 86634746, compound

Product 1

HCID 24826754HCID 24826754, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloropropan-2-one (1.01 g, 11 mmol), 1-(5-bromo-4-(2,6-difluorophenoxy)pyridin-2-yl)thiourea (3.24 g, 9.0 mmol), triethylamine (1.41 g, 14 mmol) and ethanol (15 mL) is heated at reflux for 16 hours. The reaction mixture is cooled and partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried and concentrated. The residue is purified via chromatography to afford N-(5-bromo-4-(2,6-difluorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe reaction mixture is cooled
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer is washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is purified via chromatography

Sources & evidence

ORD record
ord-309b768e64b04b10919f28689e708aa4
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…