Trifluoroacetic acid → HCID 71529262, compound
Reaction equation
[F:1][C:2]1([F:54])[CH2:7][O:6][C:5]([NH:8]C(C2C=CC(OC)=CC=2)(C2C=CC=C(OC)C=2)C2C=CC=CC=2)=[N:4][C@@:3]1([C:33]1[N:38]=[C:37]([NH:39][C:40]([C:42]2[C:47]([Cl:48])=[CH:46][C:45]([C:49]([F:52])([F:51])[F:50])=[CH:44][N:43]=2)=[O:41])[CH:36]=[CH:35][C:34]=1[F:53])[CH3:32].C(O)(C(F)(F)F)=O.[NH4+].[OH-]>ClCCl>[NH2:8][C:5]1[O:6][CH2:7][C:2]([F:54])([F:1])[C@:3]([C:33]2[N:38]=[C:37]([NH:39][C:40]([C:42]3[C:47]([Cl:48])=[CH:46][C:45]([C:49]([F:52])([F:50])[F:51])=[CH:44][N:43]=3)=[O:41])[CH:36]=[CH:35][C:34]=2[F:53])([CH3:32])[N:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Chloro-5-trifluoromethyl-pyridine-2-carboxylic acid [6-((R)-5,5-difluoro-2-{[(4-methoxy-phenyl)-(3-methoxy-phenyl)-phenyl-methyl]-amino}-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-5-fluoro-pyridin-2-yl]-amide (80 mg, 0.104 mmol) was dissolved in dichloromethane (0.1039 ml), TFA (80.0 μl, 1.04 mmol) was added and the reaction mixture was stirred at rt for 18 hours. The reaction mixture was poured onto a mixture of ice ethyl acetate and NH4OH (w=25%). The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. The crude product was chromatographed over silica gel (column 4 g, dichloromethane/methanol 95:5+0.5% ammonia) to give the title compound: 32 mg (65.9% yield).
Workup
- washThe organic layer was washed with water, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was chromatographed over silica gel (column 4 g, dichloromethane/methanol 95:5+0.5% ammonia)
Sources & evidence
- ORD record
- ord-e7fa1528823547b286de36cfb1b7e362
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163011B2
Reaction notes
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