Water → HCID 59322767, compound

HRID 450478Notes

Reaction equation

HRID 450478 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1([C:28]([O:30]C)=[O:29])[CH2:27][CH2:26]1)=[O:24].O.O.[OH-].[Li+:35]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[C:5]([F:21])=[CH:4][C:3]=1[NH:22][C:23]([C:25]1([C:28]([O-:30])=[O:29])[CH2:27][CH2:26]1)=[O:24].[Li+:35]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59322783HCID 59322783, compound

Product 1

HCID 59322767HCID 59322767, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 1-((2,5-difluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)carbamoyl)cyclopropanecarboxylate (5.8 g, 13.54 mmol) in THF (100 mL) were added water (50.0 mL) and lithium hydroxide monohydrate (2.84 g, 67.7 mmol). The reaction mixture was stirred at RT for 40 minutes. The layers were separated and the organic phase washed with brine (50 mL), dried (MgSO4) and concentrated to dryness to afford lithium 1-((2,5-difluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)carbamoyl)cyclopropanecarboxylate (5.11 g, 86% yield) as an off-white foam. MS (ESI): m/z 415.1 [M+1]+.

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fc0596a9bdbb44f68f80cd096d6f639c
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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