Methyl 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoate → 4-Methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoic acid

HRID 422559Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])=[N:17][N:16]=[CH:15]2>C1COCC1.CO>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH:22]([CH3:27])[C:23]([F:26])([F:24])[F:25])=[N:17][N:16]=[CH:15]2

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of methyl 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoate (91 mg, 243 μmol) in THF (1200 μl) and methanol (600 μl) was added NAOH (1N aqueous solution; 1215 μl, 1215 μmol) and stirred at 50° C. for 2 h, during which LC-MS indicated completion of reaction. After concentrating in vacuo, the slurry was diluted with water and the pH was adjusted with 10% aqueous HCl solution to ˜7, resulting in the precipitation of 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoic acid (86 mg, 98% yield) as a yellow solid. MS (ES+): 361.2 (M+H)+.

Workup

customcompletion of reaction
concentrationAfter concentrating in vacuo
additionthe slurry was diluted with water

Sources & evidence

ORD record: ord-512676788972491dbf8322e86c365f02
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101612B2

Reaction notes

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