Sodium Hydroxide → HCID 68516323, compound

HRID 2241267Notes

Reaction equation

HRID 2241267 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([C:40]2([C:43](=[O:52])[NH:44][C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=3)[CH2:42][CH2:41]2)=[O:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[N:12]=[C:13]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)[C:6]=12.[OH-].[Na+]>CO>[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([C:40]2([C:43](=[O:52])[NH:44][C:45]3[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=3)[CH2:42][CH2:41]2)=[O:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[N:12]=[C:13]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[C:6]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68517960HCID 68517960, compound

Product 1

HCID 68516323HCID 68516323, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved methyl 4-(4-(2-fluoro-4-(1-(4-fluorophenyl carbamoyl)cyclopropanecarboxamido)phenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzoate (230 mg, 0.327 mmol) in MeOH (5 mL) and added 10% aqueous solution of NaOH (0.65 ml, 1.63 mmol). The mixture was stirred at room temperature for 4 hours. The solvent was evaporated to a minimal volume and the crude was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer washed with brine, dried over Na2SO4 and evaporated to afford the desired product as white solid (191 mg at 90% purity, 76%) LRMS (APCI pos) m/e 690.2 (M+H).

Workup

  1. customThe solvent was evaporated to a minimal volume
  2. customthe crude was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. washThe organic layer washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-faea65b0e3fd4bd8b9c51745fe25f742
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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