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

HRID 873820Notes

Reaction equation

HRID 873820 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:11][N:12]([CH:15]3[CH2:17][CH2:16]3)[C:13]=2[CH3:14])=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:26]=[C:27]([CH3:33])[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=1>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:24][C:25]2[CH:26]=[C:27]([CH3:33])[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=2)[C:9]2[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:11][N:12]([CH:15]3[CH2:17][CH2:16]3)[C:13]=2[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-oneHCID 117702986ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 117702767ethyl 4-((4-chlorophenyl)(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-cyclopropyl-5-methyl-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-methyl-1H-pyrazole-3-carboxylate (Step 17.5) and 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2). tR: 4.59 min (HPLC 1); tR: 1.05 min (LC-MS 2); ESI-MS: 455 [M+H]+ (LC-MS 2); Rf=0.45 (CH2Cl2/MeOH 9:1).

Sources & evidence

ORD record
ord-4cea15da558c407b939c9af4ce1f3643
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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