Trifluoroacetic acid → (5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-2-oxo-1,3-oxazolidin-4-yl)methyl trifluoroacetate
Reaction equation
C(O[CH2:9][CH:10]1[CH:14]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([NH:28][C:29]4[N:34]=[C:33]([CH:35]([F:37])[F:36])[CH:32]=[CH:31][N:30]=4)[CH:22]=3)[CH:18]=[N:17]2)[O:13][C:12](=[O:38])[NH:11]1)C1C=CC=CC=1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>>[F:42][C:41]([F:44])([F:43])[C:39]([O:45][CH2:9][CH:10]1[CH:14]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([NH:28][C:29]4[N:34]=[C:33]([CH:35]([F:36])[F:37])[CH:32]=[CH:31][N:30]=4)[CH:22]=3)[CH:18]=[N:17]2)[O:13][C:12](=[O:38])[NH:11]1)=[O:40]Participants
3
Reactant 2
Product 1
Conditions
- Temperature
- 120 °C
Procedure
A solution of 4-[(benzyloxy)methyl]-5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-1,3-oxazolidin-2-one (100 mg, 0.199 mmol) in TFA (1.0 mL) was stirred and heated at 120° C. in a microwave reactor for 40 minutes. The reaction mixture was concentrated under reduced pressure to afford (5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-2-oxo-1,3-oxazolidin-4-yl)methyl trifluoroacetate, which was used in the next step without further purification. MS ESI calc'd. for C22H20F5N6O4 [M+H]+ 527. found 527.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0f0ff66185324d39ac17fd4ebb594120
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242984B2
Reaction notes
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