Lithium hydroxide, monohydrate → 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid

HRID 873795Notes

Reaction equation

HRID 873795 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:29][C:30]2[CH:35]=[CH:34][C:33](=[O:36])[N:32]([CH3:37])[CH:31]=2)[C:9]2[C:10]([C:24]([O:26]CC)=[O:25])=[N:11][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:13]=2[CH3:14])=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:29][C:30]2[CH:35]=[CH:34][C:33](=[O:36])[N:32]([CH3:37])[CH:31]=2)[C:9]2[C:10]([C:24]([OH:26])=[O:25])=[N:11][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C:13]=2[CH3:14])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117703005ethyl 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 1177027904-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a 25-mL flask was introduced ethyl 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylate (Step 1.4) (140 mg, 0.269 mmol) and LiOH.H2O (33.8 mg, 0.806 mmol) in dioxane (2.5 mL) and H2O (1.0 mL). The reaction mixture was stirred for 3 hr at rt, quenched with 0.5N HCl (50 mL), and extracted with EtOAc. The combined organic layers were washed with 0.5N HCl, dried over Na2SO4, and evaporated to dryness to afford the title product (128 mg, 0.260 mmol, 97% yield) as a green solid. tR: 3.94 min (HPLC 1); tR: 0.90 min (LC-MS 2); ESI-MS: 493 [M+H]+ (LC-MS 2).

Workup

  1. customquenched with 0.5N HCl (50 mL)
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with 0.5N HCl
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2161d2f3511a45c086b990ee54214aee
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…