Dimethylamine → HCID 86752155, compound

HRID 863701Notes

Reaction equation

HRID 863701 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[CH2:49][N:24]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:31]([C:32]3[C:33](=O)[O:34][C:35](=[O:47])[C:36]=3[C:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[N:39]([CH3:46])[CH:38]=3)=[C:23]2[CH2:22]1)(=O)C.[N:50]1C(C)=CC(C)=CC=1C.[CH3:59][NH:60][CH3:61]>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([OH:6])(=[O:5])=[O:4].[CH3:59][N:60]([CH2:20][CH:21]1[CH2:49][N:24]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:31]([C:32]3[C:33](=[O:34])[NH:50][C:35](=[O:47])[C:36]=3[C:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[N:39]([CH3:46])[CH:38]=3)=[C:23]2[CH2:22]1)[CH3:61]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 79532,4,6-TrimethylpyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10004096HCID 10004096, compound

Product 1

HCID 86752155HCID 86752155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

546 mg of trifluoromethanesulphonic anhydride in 80 ml of dichloromethane were treated at 0° C. under a nitrogen atmosphere with a suspension of 400 mg of the product of Example 19 and 208 mg of collidine in 120 ml of dichloromethane. After 1 hour, 1.9 ml of 40% aqueous dimethylamine were added and the mixture was stirred for 3 hours. The solvent was removed and the residue was subjected to chromatography on silica gel with dichloromethane/methanol/acetone (88:10:2). Trituration with ethyl acetate followed by recrystallization from methanol gave 295 mg of 3-[2,3-dihydro-2-(dimethylaminomethyl)-1H-pyrrolo[1,2-a]indol-9-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione trifluoromethanesulphonate of melting point 323°-325° C.

Workup

  1. customThe solvent was removed
  2. customTrituration with ethyl acetate followed by recrystallization from methanol

Sources & evidence

ORD record
ord-beabd9295e7e47d1b875145e56da89a1
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

Loading…