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-methyl-1H-pyrazole-3-carboxylate

HRID 873810Notes

Reaction equation

HRID 873810 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:11][N:12]([CH3:14])[CH:13]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH3:30])[C:25](=[O:29])[N:26]([CH3:28])[CH:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]2[CH:23]=[C:24]([CH3:30])[C:25](=[O:29])[N:26]([CH3:28])[CH:27]=2)[C:9]2[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:11][N:12]([CH3:14])[CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-oneHCID 117702817ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 117702706Ethyl 4-((4-chlorophenyl)((1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)amino)methyl)-1-methyl-1H-pyrazole-3-carboxylate

Procedure

The title compound was prepared in analogy to the procedure described in Step 10.3 using ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-1H-pyrazole-3-carboxylate (Step 10.2) and 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2). After purification by silica gel column chromatography, the resulting residue was further purified by preparative HPLC (Gilson gx-281; column: Sunfire C18, 30×100 mm, 5 μm; flow: 30 mL/min; gradient: 5% to 100% B in 20 min; A=0.1% TFA in H2O, B=CH3CN. detection: UV). tR: 3.91 min (HPLC 1); tR: 0.90 min (LC-MS 2); ESI-MS: 415 [M+H]+ (LC-MS 2); Rf=0.46 (CH2Cl2/MeOH 9:1).

Workup

  1. customAfter purification by silica gel column chromatography
  2. customthe resulting residue was further purified by preparative HPLC (Gilson gx-281

Sources & evidence

ORD record
ord-eff4232ad9084ffba43abb6d4fba9e7c
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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