Trimethylamine → 3-[6,7,8,9-tetrahydro-8-[(trimethylammonio)methyl]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione trifluoromethanesulfonate

HRID 863668Notes

Reaction equation

HRID 863668 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].C(O[CH2:20][CH:21]1[CH2:50][CH2:49][N:24]2[C:25]3[C:30]([C:31]([C:32]4[C:33](=O)[O:34][C:35](=[O:47])[C:36]=4[C:37]4[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]([CH3:46])[CH:38]=4)=[C:23]2[CH2:22]1)=[CH:29][CH:28]=[CH:27][CH:26]=3)(=O)C.[N:51]1C(C)=CC(C)=CC=1C.[CH3:60][N:61]([CH3:63])[CH3:62]>ClCCl.C(O)C>[F:1][C:2]([F:15])([F:14])[S:3]([O-:6])(=[O:5])=[O:4].[CH3:60][N+:61]([CH2:20][CH:21]1[CH2:50][CH2:49][N:24]2[C:25]3[C:30]([C:31]([C:32]4[C:33](=[O:34])[NH:51][C:35](=[O:47])[C:36]=4[C:37]4[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]([CH3:46])[CH:38]=4)=[C:23]2[CH2:22]1)=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH3:63])[CH3:62]

Participants

7

Reactant 4

HCID 1146TrimethylamineHCID 79532,4,6-TrimethylpyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 103898823-[8-(Acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione

Product 1

HCID 103264883-[6,7,8,9-tetrahydro-8-[(trimethylammonio)methyl]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

265 mg of trifluoromethanesulfonic anhydride in 40 ml of dichloromethane were treated at 0° C. under a nitrogen atmosphere with a suspension of 200 mg of the pyrroledione product of Example 1 and 100 mg of collidine in 30 ml of dichloromethane. After 5 hours, 0.5 ml of a 33% solution of trimethylamine in ethanol was added and the mixture was stirred for 18 hours. The resulting precipitate was filtered off and dried to give 237 mg of 3-[6,7,8,9-tetrahydro-8-[(trimethylammonio)methyl]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione trifluoromethanesulfonate of melting point 320°-324° C.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-0e1c304181fa409bafe27958c63238bb
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

Loading…