Potassium Carbonate → 4-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyrazole-1-carboxylic acid phenyl ester

HRID 60096Notes

Reaction equation

HRID 60096 reaction equation
[F:1][C:2]1[C:7]([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[N:21][NH:22][CH:23]=4)[CH:17]=3)[NH:12][CH:11]=2)=[O:9])=[C:6]([F:24])[CH:5]=[CH:4][C:3]=1[NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27].C(=O)([O-])[O-].[K+].[K+].[C:38](Cl)(=[O:46])[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(#N)C>[C:40]1([O:39][C:38]([N:21]2[CH:20]=[C:19]([C:16]3[CH:17]=[C:18]4[C:10]([C:8](=[O:9])[C:7]5[C:6]([F:24])=[CH:5][CH:4]=[C:3]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[C:2]=5[F:1])=[CH:11][NH:12][C:13]4=[N:14][CH:15]=3)[CH:23]=[N:22]2)=[O:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 49779453Propane-1-sulfonic acid{2,4-difluoro-3-[5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide

Product 1

HCID 532620384-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyrazole-1-carboxylic acid phenyl esterYield 6.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a reaction vial, propane-1-sulfonic acid {2,4-difluoro-3-[5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide (23, 7 mg, 0.02 mmol) is dissolved in 0.05 mL of acetonitrile and potassium carbonate (4 mg, 0.03 mmol) and carbonochloridic acid, phenyl ester (24, 0.0025 mL, 0.02 mmol) are added and the reaction is stirred at room temperature overnight. The reaction is concentrated under vacuum and the resulting material is purified by reverse phase HPLC to provide the desired compound (P-1016, 0.7 mg).

Workup

  1. concentrationThe reaction is concentrated under vacuum
  2. customthe resulting material is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2fb99741025446c29b031965c54709ed
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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