Methanol → Trifluoroacetic acid

HRID 2207431Notes

Reaction equation

HRID 2207431 reaction equation
[OH-:1].[Na+].[CH3:3][OH:4].[CH3:5][C:6]1[CH:7]=[C:8]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[N:30]=[N:31][N:32]([CH2:34][C:35]([O:37]C)=[O:36])[CH:33]=3)=[N:27][CH:28]=2)[CH:9]=[C:10]([NH:12][C:13]2[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=2)[CH:11]=1>C1COCC1>[CH3:5][C:6]1[CH:7]=[C:8]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[N:30]=[N:31][N:32]([CH2:34][C:35]([OH:37])=[O:36])[CH:33]=3)=[N:27][CH:28]=2)[CH:9]=[C:10]([NH:12][C:13]2[N:18]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:16]=[CH:15][N:14]=2)[CH:11]=1.[C:3]([OH:4])([C:19]([F:22])([F:21])[F:20])=[O:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 118103403HCID 118103403, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 118092595HCID 118092595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (1 M, 0.55 mL, 0.550 mmol) and methanol (1.5 mL) was added to a solution of methyl {4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]-1H-1,2,3-triazol-1-yl}acetate (55.0 mg, 0.094 mmol) in THF (1.5 mL). The mixture was stirred at room temperature for 3 hours and then directly purified by reverse phase HPLC to afford {4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]-1H-1,2,3-triazol-1-yl}acetic acid as a TFA salt. MS APCI C21H17F3N7O2 [M+H]456. found 456. 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H), 8.85 (d, J=17.2 Hz, 2H), 8.63 (s, 1H), 8.12 (s, 2H), 8.02 (s, 1H), 7.57 (s, 1H), 7.27 (d, J=13.2 Hz, 2H), 5.36 (s, 2H), 2.37 (s, 3H).

Workup

  1. customdirectly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ef0f5383e21e4ff8931296b4fb263991
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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