Pyridine → Methyl 4-{[(3-bromo-2,6-dichlorophenyl)acetyl]amino}-1,3-thiazole-5-carboxylate

HRID 625669Notes

Reaction equation

HRID 625669 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[Br:17][C:18]1[C:19]([Cl:29])=[C:20]([CH2:25][C:26](Cl)=[O:27])[C:21]([Cl:24])=[CH:22][CH:23]=1>C(#N)C>[Br:17][C:18]1[C:19]([Cl:29])=[C:20]([CH2:25][C:26]([NH:1][C:2]2[N:3]=[CH:4][S:5][C:6]=2[C:7]([O:9][CH3:10])=[O:8])=[O:27])[C:21]([Cl:24])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15832487Methyl 4-amino-1,3-thiazole-5-carboxylateHCID 89826315(3-Bromo-2,6-dichlorophenyl)acetyl chloride

Product 1

HCID 89826116Methyl 4-{[(3-bromo-2,6-dichlorophenyl)acetyl]amino}-1,3-thiazole-5-carboxylateYield 74.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2.0 g (12.64 mmol) of methyl 4-amino-1,3-thiazole-5-carboxylate were dissolved in 20 acetonitrile, and 2.05 ml (25.29 mmol) of pyridine were added. After 5 min of stirring at room temperature, a solution of 4.21 g (13.91 mmol) of (3-bromo-2,6-dichlorophenyl)acetyl chloride (obtained from (3-bromo-2,6-dichlorophenyl)acetic acid, see WO9736868) in 10 ml of acetonitrile was added dropwise. The reaction mixture was stirred at RT for 12 h. The precipitate formed was filtered off, washed with water and dried under reduced pressure. The resulting mother liquor was concentrated by evaporation, dissolved in chloroform and chromatographed (ethyl acetate/n-heptane: 20/80 to 80/20). This gives a total of 4.01 g of methyl 4-{[(3-bromo-2,6-dichlorophenyl)acetyl]amino}-1,3-thiazole-5-carboxylate.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at RT for 12 h
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried under reduced pressure
  7. concentrationThe resulting mother liquor was concentrated by evaporation
  8. dissolutiondissolved in chloroform
  9. customchromatographed (ethyl acetate/n-heptane: 20/80 to 80/20)

Sources & evidence

ORD record
ord-aeb6e577d59644fba9c64568a8b2dd70
Source dataset
uspto-grants-2016_04
Patent number
US09307767B2

Reaction notes

Loading…