Trifluoroacetic acid → Trifluoroacetic acid
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH:11]1[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1)[C:5]#[N:6].[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21].COC(=O)C1C=CC(NC2CC3N(C)C(CC3)C2)=C(O)C=1.F[C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([O:55][CH3:56])[C:50]=1[N+]([O-])=O.FC1C=CC=CC=1[N+]([O-])=O>>[CH3:56][O:55][C:51]1[CH:52]=[CH:53][CH:54]=[C:49]2[C:50]=1[O:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[N:10]2[CH:11]1[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]Participants
7
Reactant 5
Product 2
Procedure
Using an adaptation of Procedure 2, substituting the TFA salt of 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile, 2p for the TFA salt of 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzoic acid methyl ester, 1a, and 1-fluoro-3-methoxy-2-nitrobenzene, 1e for 2-fluoronitrobenzene, the title compound 6-methoxy-10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carbonitrile, 3p 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=362 (M+1).
Sources & evidence
- ORD record
- ord-24029bed7cf84186a1b7d747051f0778
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652005B2
Reaction notes
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