Trifluoroacetic acid → Trifluoroacetic acid
Reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].COC(=O)C1C=CC(N[CH:18]2[CH2:24][CH:23]3[N:25]([CH3:26])[CH:20]([CH2:21][CH2:22]3)[CH2:19]2)=C(O)C=1.F[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:31]=1[N+:38]([O-])=O.FC1C=CC=C[C:43]=1[N+:48]([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>>[CH3:37][O:36][C:32]1[CH:33]=[C:34]([CH:35]=[CH:30][C:31]=1[NH:38][CH:18]1[CH2:24][CH:23]2[N:25]([CH3:26])[CH:20]([CH2:21][CH2:22]2)[CH2:19]1)[C:43]#[N:48].[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]Participants
8
Reactant 6
Product 2
Procedure
Using an adaptation of Procedure 2, substituting 8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamine for the TFA salt of 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzoic acid methyl ester, 1a, 1-fluoro-3-methoxy-2-nitrobenzene, 1e for 2-fluoronitrobenzene, and cesium carbonate for potassium carbonate, the title compound 3-methoxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile, 1p 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=272 (M+1).
Sources & evidence
- ORD record
- ord-5a32da4b4647401eafd9711c591fd798
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652005B2
Reaction notes
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