Sodium Hydroxide → HCID 73437650, compound

HRID 1056590Notes

Reaction equation

HRID 1056590 reaction equation
[P:1]([OH:39])([OH:38])([O:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:13]=[C:8]2[C:7]([C:21](=[O:37])[C:22]2[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=2[F:36])=[CH:6]1)=[O:2].[OH-].[Na+:41]>C1COCC1.O>[P:1]([O-:38])([O-:39])([O:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:13]=[C:8]2[C:7]([C:21](=[O:37])[C:22]2[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=2[F:36])=[CH:6]1)=[O:2].[Na+:41].[Na+:41]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 73388277(5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl dihydrogen phosphate

Product 1

HCID 73437650HCID 73437650, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl dihydrogen phosphate (396 mg, 0.66 mmol) in THF (20 mL) was added dropwise a solution of NaOH (58 mg, 1.45 mmol) in 0.3 mL of H2O and 4 mL of THF at rt. The reaction was stirred at rt for 4 h, and then filtered to give the title compound as a white solid (401 mg, 94.4%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-bde60975e8e94ad59c9e16a485060ddb
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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