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

HRID 873804Notes

Reaction equation

HRID 873804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:11][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:31]=[C:32]([Cl:38])[C:33](=[O:37])[N:34]([CH3:36])[CH:35]=1>C(Cl)Cl.CO>[Cl:38][C:32]1[C:33](=[O:37])[N:34]([CH3:36])[CH:35]=[C:30]([NH:29][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]2[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:11][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=2)[CH:31]=1

Participants

4

Reactant 2

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-oneHCID 117702731ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 117702694ethyl 4-((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)(4-chlorophenyl)methyl)-1-(4-methoxybenzyl)-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 1.4 using ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate (Step 9.3) and 5-amino-3-chloro-1-methylpyridin-2(1H)-one (Step 5.2). tR: 4.91 min (HPLC 1); tR: 1.08 min (LC-MS 2); ESI-MS: 541/543 [M+H]+ (LC-MS 2); Rf=0.32 (CH2Cl2/MeOH 9:1).

Sources & evidence

ORD record
ord-c77cd23273e945a389cd0506d8e9bbb1
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…