Sodium Hydroxide → HCID 71554489, compound

HRID 1776422Notes

Reaction equation

HRID 1776422 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[N:27]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[C:25]([O:35][CH3:36])=[CH:24][N:23]=3)=[N:14]2)=[C:10]([Cl:37])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[N:27]=[C:26]([NH:28][C:29]4[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=4)[C:25]([O:35][CH3:36])=[CH:24][N:23]=3)=[N:14]2)=[C:10]([Cl:37])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71553532HCID 71553532, compound

Product 1

HCID 71554489HCID 71554489, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 g of methyl 2,4-dichloro-3-({3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-1H-indazol-1-yl}methyl)benzoate (2-16-1, 1.868 mmol, 1. eq.) were dissolved in 19 ml of dry THF and 2.2 ml of methanol. 4.67 ml of 2 M aqueous sodium hydroxide solution (9.34 mmol, 5 eq.) were added. The mixture was stirred for three hours at room temperature. The reaction mixture was partitioned between citric acid (pH 3) and ethyl acetate. This process dropped out a white precipitate which was filtered off and dried for three days to yield 992 mg (1.86 mmol, 99.8%) of the analytically pure target compound.

Workup

  1. customThe reaction mixture was partitioned between citric acid (pH 3) and ethyl acetate
  2. additionThis process dropped out a white precipitate which
  3. filtrationwas filtered off
  4. customdried for three days
  5. customto yield 992 mg (1.86 mmol, 99.8%) of the analytically pure target compound

Sources & evidence

ORD record
ord-379d77df059543969cd85485487330c5
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

Loading…