Phenacyl bromide → 1-(5-Bromo-4-(4-phenylthiazol-2-yl)pyridin-2-yl)-3-ethylurea

HRID 2243076Notes

Reaction equation

HRID 2243076 reaction equation
[Br:1][C:2]1[C:3]([C:14](=[S:16])[NH2:15])=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>C(#N)C>[Br:1][C:2]1[C:3]([C:14]2[S:16][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:15]=2)=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 59208439AZD7118 Bromo Thioamide2×

Product 1

HCID 592085041-(5-Bromo-4-(4-phenylthiazol-2-yl)pyridin-2-yl)-3-ethylureaYield 84.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 42, 0.146 g, 0.48 mmol) in acetonitrile (3 mL), 2-bromo-1-phenylethanone (0.105 g, 0.53 mmol) was added and the reaction mixture was heated to 80° for 16 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting solids were filtered and washed with acetonitrile to yield 164 mg of the title compound as an off-white solid.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated to 80° for 16 h
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe resulting solids were filtered
  5. washwashed with acetonitrile

Sources & evidence

ORD record
ord-5f795704f2194ca29e815cfebf151739
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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