Ammonia → Bisindolylmaleimide X hydrochloride

HRID 863667Notes

Reaction equation

HRID 863667 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.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.[NH3:60].[Cl:61]CCl>>[ClH:61].[NH2:60][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

Participants

6

Reactant 5

HCID 222AmmoniaHCID 6344Dichloromethane2×HCID 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 11539879Bisindolylmaleimide X hydrochloride

Conditions

Temperature
10 °C

Procedure

2.50 g of trifluoromethanesulfonic anhydride in 330 ml of dichloromethane were treated at 0° C. under a nitrogen atmosphere with a suspension of 1.87 g of the pyrroledione product of Example 1 and 0.94 g of collidine in 280 ml of dichloromethane. After 2.5 hours, the mixture was allowed to warm to 10° C. Then, 37 ml of 33% aqueous ammonia were added and the mixture was allowed to warm to room temperature overnight. The mixture was washed with water, dried and evaporated. The residue was subjected to chromatography on silica gel with dichloromethane/methanol/acetic acid/water (90:18:3:2). The combined product-containing fractions were treated with 2M hydrochloric acid and evaporated to give 930 mg of 3-[8-(aminomethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione hydrochloride of melting point 310°-313° C.

Workup

  1. temperatureto warm to room temperature overnight
  2. washThe mixture was washed with water
  3. customdried
  4. customevaporated
  5. additionThe combined product-containing fractions
  6. additionwere treated with 2M hydrochloric acid
  7. customevaporated

Sources & evidence

ORD record
ord-ec06762f6fcf445e954391d79354fb9a
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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