Trifluoroacetic acid → Trifluoroacetic acid
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[NH:25][C:24](=[O:26])[O:23][N:22]=4)=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:3][CH2:2]1.C(O)([C:29]([F:32])([F:31])[F:30])=O.N1CCC(N2C3C=CC(C4NN=NN=4)=CC=3OC3C2=CC=CC=3)CC1.[CH:59]1[CH:64]=[C:63]([CH:65]=O)[N:62]=[CH:61][CH:60]=1.N1C=CN=C1C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>>[N:62]1[CH:61]=[CH:60][CH:59]=[CH:64][C:63]=1[CH2:65][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[NH:25][C:24](=[O:26])[O:23][N:22]=4)=[CH:16][C:15]=3[O:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][CH2:6]1.[C:24]([OH:23])([C:29]([F:32])([F:31])[F:30])=[O:26]Participants
9
Reactant 7
Product 2
Procedure
Using an adaptation of the method described in Procedure 7, substituting the TFA salt of 3-(10-piperidin-4-yl-10H-phenoxazin-3-yl)-4H-[1,2,4]oxadiazol-5-one, 2b for the TFA salt of 10-piperidin-4-yl-3-(1H-tetrazol-5-yl)-10H-phenoxazine, 6a, 2-pyridylcarboxaldehyde for 1H-imidazole-2-carboxaldehyde and sodium triacetoxyborohydride for tetramethylammonium triacetoxyborohydride, the title compound 3-[10-(1-pyridin-2-ylmethyl-piperidin-4-yl)-10H-phenoxazin-3-yl]-4H-[1,2,4]oxadiazol-5-one, 6b was obtained as a TFA salt after purification via reverse phase HPLC (eluent: CH3CN in H2O containing 0.1% TFA). MS m/z (MH+) 441.9.
Sources & evidence
- ORD record
- ord-87fc064b363a44659f8303ba772fad18
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432257B2
Reaction notes
Loading…