5-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one → ethyl 4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)-methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate

HRID 873865Notes

Reaction equation

HRID 873865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11][N:12]([CH:18]3[CH2:20][CH2:19]3)[C:13]=2[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:29]=[C:30]([Cl:36])[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=1>CO.C(Cl)Cl>[Cl:36][C:30]1[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=[C:28]([NH:27][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]2[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11][N:12]([CH:18]3[CH2:20][CH2:19]3)[C:13]=2[C:14]([F:17])([F:16])[F:15])[CH:29]=1

Participants

4

Reactant 2

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-oneHCID 117702816ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-Pyrazole-3-carboxylate

Product 1

HCID 117702576ethyl 4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)-methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 10.3 using ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate (Step 40.2) and 5-amino-3-chloro-1-methylpyridin-2(1H)-one (Step 5.2) at RT for 3 days. tR: 1.24 min (LC-MS 2); ESI-MS: 529 [M+H]+ (LC-MS 2); Rf=0.52 (5% MeOH/CH2Cl2).

Sources & evidence

ORD record
ord-bcdd115c4d934bb7b02bdc3c04f9d6fd
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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