2-Acetamidopyridine → 2-[(2-chloro-3-methyl-1-oxobutyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene propanamide

HRID 648474Notes

Reaction equation

HRID 648474 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].C([Li])CCC.[Cl:16][CH:17]([C:21]1[O:26][C:25](=[O:27])[C:24]2[CH:28]=[CH:29][CH:30]=[C:31]([C:32]([F:35])([F:34])[F:33])[C:23]=2[N:22]=1)[CH:18]([CH3:20])[CH3:19]>CCCCCC>[Cl:16][CH:17]([CH:18]([CH3:20])[CH3:19])[C:21]([NH:22][C:23]1[C:31]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](=[O:27])[CH2:2][C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:3])=[O:26]

Participants

5

Reactant 3

HCID 729292-AcetamidopyridineHCID 136556172-(1-chloro-2-methylpropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-oneHCID 178418339Butyllithium

Product 1

HCID 141405942-[(2-chloro-3-methyl-1-oxobutyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene propanamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using the procedure of Step A of Example 13, 10.16 g of 2-acetylaminopyridine, 106 ml of a hexane solution of n-butyllithium (1,4M) and 11.4 g of 2-(1-chloro-2-methylpropyl)-8-trifluoromethyl-4H-3,1-benzoxazin-4-one of Step A of example 3 were reacted to obtain 11.8 g of 2-[(2-chloro-3-methyl-1-oxobutyl)-amino]-β-oxo-N-(2-pyridinyl)-3-trifluoromethyl-benzene propanamide melting at 136°-138° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-54386c83b42641d088fd9d30ae964446
Source dataset
uspto-grants-1988_04
Patent number
US04735951

Reaction notes

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