Methanol → HCID 72703836, compound

HRID 2207426Notes

Reaction equation

HRID 2207426 reaction equation
[OH-].[Na+].CO.[F:5][C:6]([F:38])([CH:12]([OH:37])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([NH:25][C:26]3[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=3)[CH:22]=[C:21]([CH3:36])[CH:20]=2)=[CH:15][N:14]=1)[C:7]([O:9]CC)=[O:8]>C1COCC1>[F:38][C:6]([F:5])([CH:12]([OH:37])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([NH:25][C:26]3[N:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][N:27]=3)[CH:22]=[C:21]([CH3:36])[CH:20]=2)=[CH:15][N:14]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 118093050HCID 118093050, compound

Product 1

HCID 72703836HCID 72703836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydroxide (1 M, 0.190 mL, 0.190 mmol) and methanol (0.300 mL) were added to a solution of ethyl 2,2-difluoro-3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate (17.8 mg, 0.037 mmol) in THF (0.500 mL). The mixture was stirred at 40° C. for 2 hours and then cooled to room temperature and the crude reaction mixture was directly purified by reverse phase HPLC to afford 2,2-difluoro-3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoic acid. MS APCI C20H16F5N4O3 [M+H]455. found 455.0. 1H NMR (500 MHz, DMSO-d6)) δ10.28 (s, 1H), 8.83 (d, J=5.3 Hz, 1H), 8.74 (d, J=2.2 Hz, 1H), 8.08 (d, J=11.1 Hz, 1H), 7.96 (s, 1H), 7.66 (d, J=8.7 Hz, 1H), 7.58 (s, 1H), 7.27 (d, J=5.2 Hz, 1H), 7.21 (s, 1H), 5.17 (t, J=12.7 Hz, 1H), 2.36 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. customthe crude reaction mixture
  3. customwas directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-97f420bc8dc146b8b066f66cd9a52fe0
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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