Trifluoroacetic acid → 10-(8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide
Reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][CH:12]([N:17]1[C:30]3[CH:29]=[CH:28][C:27]([C:31](O)=[O:32])=[CH:26][C:25]=3[O:24][C:23]3[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:58]([N:60](CC)[CH2:61][CH3:62])[CH3:59]>CN(C=O)C>[CH2:58]([N:60]([CH2:61][CH3:62])[C:31]([C:27]1[CH:28]=[CH:29][C:30]2[N:17]([CH:12]3[CH2:13][CH:14]4[N:9]([CH3:8])[CH:10]([CH2:16][CH2:15]4)[CH2:11]3)[C:18]3[C:23]([O:24][C:25]=2[CH:26]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:32])[CH3:59]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the TFA salt of 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid 3a (65 mg, 0.14 mmol) and HBTU (64 mg; 0.17 mmol) in DMF (2 mL) was added triethylamine (69 μL, 0.43 mmol). The mixture was stirred for 1 hr at rt, and purified without prior quenching via reverse phase HPLC (eluent gradient: acetonitrile in water containing 0.1% TFA) to yield 44.4 mg (61%) of title compound 10-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenoxazine-3-carboxylic acid diethylamide, 4a as a TFA salt. MS m/z (MH+) 406.2.
Workup
- custompurified
- customwithout prior quenching via reverse phase HPLC (eluent gradient: acetonitrile in water containing 0.1% TFA)
Sources & evidence
- ORD record
- ord-1e292f2caec44cbd923efb87dfeb4143
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652005B2
Reaction notes
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