1-Bromo-2-butanone → 1-(5-Bromo-4-(4-ethylthiazol-2-yl)pyridin-2-yl)-3-ethylurea

HRID 2243064Notes

Reaction equation

HRID 2243064 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](=O)[CH2:20][CH3:21]>C(O)C>[Br:1][C:2]1[C:3]([C:14]2[S:16][CH:18]=[C:19]([CH2:20][CH3:21])[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 131561-Bromo-2-butanoneHCID 59208439AZD7118 Bromo Thioamide2×

Product 1

HCID 592083161-(5-Bromo-4-(4-ethylthiazol-2-yl)pyridin-2-yl)-3-ethylureaYield 36.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 42, 1 g, 3.30 mmol) in ethanol (25 mL), 1-bromobutan-2-one (0.337 mL, 3.30 mmol) was added, and the reaction mixture was heated to 80° for 4 h, then cooled to room temperature, concentrated under reduced pressure, and the resulting solid was washed with acetonitrile to give the title compound as an off-white solid (431 mg). MS (ESP): 356 (M+1) for C13H15BrN4OS; NMR: 1.09 (t, 3H); 1.29 (t, 3H); 2.84 (q, 2H); 3.15-3.20 (m, 2H); 7.34 (br s, 1H); 7.66 (s, 1H); 8.38 (s, 1H); 8.50 (s, 1H); 9.36 (s, 1H).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated to 80° for 4 h
  3. concentrationconcentrated under reduced pressure
  4. washthe resulting solid was washed with acetonitrile

Sources & evidence

ORD record
ord-ccf7f579f7cf465da53684e75e212c32
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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