2,4,6-Trimethylpyridine → 3-[6,7,8,9-tetrahydro-8-[(1-piperidino)methyl]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione
Reaction equation
C(O[CH2:5][CH:6]1[CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=O)[O:19][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=O)C.[N:36]1C(C)=CC(C)=CC=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>ClCCl>[N:60]1([CH2:5][CH:6]2[CH2:35][CH2:34][N:9]3[C:10]4[C:15]([C:16]([C:17]5[C:18](=[O:19])[NH:36][C:20](=[O:32])[C:21]=5[C:22]5[C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[N:24]([CH3:31])[CH:23]=5)=[C:8]3[CH2:7]2)=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 0.64 g of the product of Example 1 and 0.4 ml of 2,4,6-collidine in 20 ml of dichloromethane was added dropwise to a solution of 0.75 g of trifluoromethanesulfonic anhydride in 10 ml of dichloromethane at 0° C. After 2.5 hours, the mixture was treated with 3 ml of piperidine and stirred for 16 hours. Concentration and chromatography of the residue on silica gel with dichloromethane/methanol (gradient from 98:2 to 50:50) gave 340 mg of 3-[6,7,8,9-tetrahydro-8-[(1-piperidino)methyl]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione. This was converted into the hydrochloride of melting point 294° C. (decomposition), by treatment with a saturated solution of hydrogen chloride in ethyl acetate.
Workup
- concentrationConcentration and chromatography of the residue on silica gel with dichloromethane/methanol (gradient from 98:2 to 50:50)
Sources & evidence
- ORD record
- ord-c76cc6886acc4d7ea00b6c6fd876e821
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05721245
Reaction notes
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