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

HRID 873849Notes

Reaction equation

HRID 873849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[CH:10]=[N:11][N:12]([CH:19]3[CH2:21][CH2:20]3)[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:25]=[C:26]([CH3:32])[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=1>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:23][C:24]2[CH:25]=[C:26]([CH3:32])[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=2)[C:9]2[CH:10]=[N:11][N:12]([CH:19]3[CH2:21][CH2:20]3)[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-oneHCID 117702623ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-1H-pyrazole-5-carboxylate

Product 1

HCID 117702755ethyl 4-((4-chlorophenyl)((1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)amino)methyl)-1-cyclopropyl-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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-1H-pyrazole-5-carboxylate (Step 34.3) and 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2). tR: 4.78 min (HPLC 1); tR: 1.10 min (LC-MS 2); ESI-MS: 441 [M+H]+ (LC-MS 2); Rf=0.31 (EtOAc).

Sources & evidence

ORD record
ord-16352a3345eb4b64a699a1215b859631
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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