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

HRID 2061851Notes

Reaction equation

HRID 2061851 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(#N)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-ethylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 3, 6.06 g, 20 mmol) was suspended in acetonitrile (150 ml). 1-Bromobutan-2-one (30 mmol) was added and the reaction mixture was heated at reflux for 16 h. The reaction was cooled to 0° C. and the suspension was filtered. The solid was washed with acetonitrile (50 ml), collected, and dried in a vacuum oven at 50° C. for 4 hours to give an off white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationthe suspension was filtered
  4. washThe solid was washed with acetonitrile (50 ml)
  5. customcollected
  6. customdried in a vacuum oven at 50° C. for 4 hours
  7. customto give an off white solid

Sources & evidence

ORD record
ord-9e328f0b41964bdca9d76383110cbb36
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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