Methanol → Trifluoroacetic acid

HRID 2207424Notes

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

Participants

Reactant 4

HCID 887Methanol

HCID 8028Tetrahydrofuran

HCID 14798Sodium Hydroxide

HCID 131735917HCID 131735917, compound

Product 2

HCID 6422Trifluoroacetic acid

HCID 72703838HCID 72703838, compound

Procedure

Sodium hydroxide (1 M, 0.65 mL) and methanol (0.800 mL) were added to a solution of 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbaldehyde (60.0 mg, 0.130 mmol) in THF (1.00 mL) and the mixture was stirred at room temperature for 2 hours. The mixture was directly purified on reverse phase HPLC to afford 3-hydroxy-2,2-dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoic acid as a TFA salt. MS APCI C22H22F3N4O3 [M+H]447. found 447. 1H NMR (500 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.83 (d, J=5.2 Hz, 1H), 8.75 (d, J=2.6 Hz, 1H), 8.21 (d, J=7.5 Hz, 1H), 7.97 (s, 1H), 7.69 (d, J=8.0 Hz, 1H), 7.58 (s, 1H), 7.27 (d, J=5.1 Hz, 1H), 7.24 (s, 1H), 5.01 (s, 1H), 2.36 (s, 3H), 1.05 (s, 3H), 0.99 (s, 3H).

Workup

customThe mixture was directly purified on reverse phase HPLC

Sources & evidence

ORD record: ord-ba41c8af73d24fe98a8a1d128d0216b3
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376418B2

Reaction notes

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