Thiourea → 5-[2-Amino-5-(4-chlorophenyl)-1,3-thiazol-4-yl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)-phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 1672596Notes

Reaction equation

HRID 1672596 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH:6]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:7]([C:9]1[CH:10]=[C:11]([C:27]([NH:29][CH3:30])=[O:28])[C:12](=[O:26])[N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:14]=1[CH3:15])=O>C(#N)C>[NH2:1][C:2]1[S:3][C:6]([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)=[C:7]([C:9]2[CH:10]=[C:11]([C:27]([NH:29][CH3:30])=[O:28])[C:12](=[O:26])[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[CH:17]=3)[C:14]=2[CH3:15])[N:4]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 866304695-[bromo(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 248305095-[2-Amino-5-(4-chlorophenyl)-1,3-thiazol-4-yl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)-phenyl]-1,2-dihydropyridine-3-carboxamideYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

Thiourea (8.5 mg, 0.11 mmol) was added to 5-[bromo(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (SM4, mg, 55 mmol) in acetonitrile (1 ml) and the mixture was heated in a microwave oven to 120° C. for 10 min. The crude product was purified on an Xterra C8 column using a gradient of acetonitrile/water. Freeze drying of the mixture afforded the title compound (10 mg, 35%).

Workup

  1. customThe crude product was purified on an Xterra C8 column
  2. customFreeze drying of the mixture

Sources & evidence

ORD record
ord-0380bfc6c0c1460eb275977d165772d5
Source dataset
uspto-grants-2011_08
Patent number
US07998984B2

Reaction notes

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