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

HRID 873839Notes

Reaction equation

HRID 873839 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:11][N:12]([CH3:15])[C:13]=2[CH3:14])=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([F:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=1>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:22][C:23]2[CH:24]=[C:25]([F:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=2)[C:9]2[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:11][N:12]([CH3:15])[C:13]=2[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1177026115-amino-3-fluoro-1-methylpyridin-2(1H)-oneHCID 117702851ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1,5-dimethyl-1H-pyrazole-3-carboxylate

Product 1

HCID 117703080ethyl 4-((4-chlorophenyl)(5-fluoro-1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1,5-dimethyl-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)-1,5-dimethyl-1H-pyrazole-3-carboxylate (Step 28.2) and 5-amino-3-fluoro-1-methylpyridin-2(1H)-one (Step 14.2). tR: 4.17 min (HPLC 1); tR: 0.93 min (LC-MS 2); ESI-MS: 433 [M+H]+ (LC-MS 2); Rf=0.77 (CH2Cl2/MeOH 9:1).

Sources & evidence

ORD record
ord-3381bcdf093b41c3a5f6f14639142761
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…