Lithium hydroxide, monohydrate → 4-((4-chlorophenyl)((4-methoxybenzyl)amino)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylic acid

HRID 873826Notes

Reaction equation

HRID 873826 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:9]2[C:10]([CH3:20])=[N:11][N:12]([CH:17]3[CH2:19][CH2:18]3)[C:13]=2[C:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C:9]2[C:10]([CH3:20])=[N:11][N:12]([CH:17]3[CH2:18][CH2:19]3)[C:13]=2[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1317325704-((4-chlorophenyl)((4-methoxybenzyl)amino)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 1177028014-((4-chlorophenyl)((4-methoxybenzyl)amino)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a 100-mL flask was introduced 4-((4-chlorophenyl)((4-methoxybenzyl)amino)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylate (Step 23.6) (2.22 g, 4.89 mmol) and LiOH.H2O (0.616 g, 14.67 mmol) in dioxane (15 mL) and H2O (6 mL). The reaction mixture was stirred for hr at rt, quenched with 0.5N HCl (100 mL), and diluted with EtOAc (100 mL). The resulting suspension was filtered to afford the title compound (2.30 g, 4.59 mmol, 94% yield) as a colorless solid. tR: 3.86 min (HPLC 1); tR: 0.87 min (LC-MS 2); ESI-MS: 426 [M+H]+ (LC-MS 2).

Workup

  1. customquenched with 0.5N HCl (100 mL)
  2. additiondiluted with EtOAc (100 mL)
  3. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-4d95013f402c449386d7399d893a00a0
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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