Sodium Hydroxide → HCID 118092592, compound

HRID 2207368Notes

Reaction equation

HRID 2207368 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH2:31][C:32]([O:34]C)=[O:33])(=[O:30])=[O:29])=[N:25][CH:26]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=2)[CH:9]=1>C(O)C>[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH2:31][C:32]([OH:34])=[O:33])(=[O:29])=[O:30])=[N:25][CH:26]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][N:12]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131735892HCID 131735892, compound

Product 1

HCID 118092592HCID 118092592, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (1.00 mL) and aqueous sodium hydroxide (1 M, 0.075 mL, 0.075 mmol) were added to methyl {[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]sulfamoyl}acetate (TFA salt, 20.0 mg, 0.034 mmol) and stirred at room temperature for 45 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by reverse phase chromatography (10-80% acetonitrile in water+0.1% TFA) to give {[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]sulfamoyl}acetic acid (TFA salt) as a colorless solid. MS APCI calc'd for C19H17F3N5O4S [M+H]+ 468. found 468. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.83 (d, J=5.2 Hz, 1H), 8.54-8.21 (m, 1H), 8.00 (s, 1H), 7.88 (s, 1H), 7.53 (s, 1H), 7.27 (d, J=5.1 Hz, 1H), 7.14 (s, 2H), 4.38-3.68 (m, 2H), 2.34 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by reverse phase chromatography (10-80% acetonitrile in water+0.1% TFA)

Sources & evidence

ORD record
ord-d223833f9f514dcab27daf3ba36edd4c
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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