Trifluoroacetic acid → Trifluoroacetic acid
Reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C[O:9][C:10]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[CH:14]=[C:15]([C:33]#[N:34])[CH:16]=[CH:17][C:18]=1[N:19]2[CH:24]1[CH2:30][CH:29]2[N:31]([CH3:32])[CH:26]([CH2:27][CH2:28]2)[CH2:25]1.C(N(CC)C(C1C=CC2N(C3CC4N(CCC5C=CC=CC=5)C(CC4)C3)C3C(OC=2C=1)=C(OC)C=CC=3)=O)C>>[OH:9][C:10]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[CH:14]=[C:15]([C:33]#[N:34])[CH:16]=[CH:17][C:18]=1[N:19]2[CH:24]1[CH2:30][CH:29]2[N:31]([CH3:32])[CH:26]([CH2:27][CH2:28]2)[CH2:25]1.[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]Participants
5
Reactant 3
Product 2
Procedure
Using an adaptation of Procedure 13, substituting the TFA salt of 6-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carbonitrile, 3p for the TFA salt of 6-methoxy-10-(8-phenethyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 6e, the title compound 6-hydroxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carbonitrile, 4p was obtained as TFA salt and as a mixture of endo and exo isomers after purification via reverse phase HPLC (eluent gradient: 20% to 45% CH3CN in water containing 0.1% TFA). MS m/z=348 (M+1).
Sources & evidence
- ORD record
- ord-59fef76d87294ac0942f4604678faa26
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652005B2
Reaction notes
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