Hydrochloric Acid → Bisindolylmaleimide XI hydrochloride

HRID 863670Notes

Reaction equation

HRID 863670 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.[CH3:60][NH:61][CH3:62].[ClH:63]>ClCCl.C(O)C.C(OCC)(=O)C>[ClH:63].[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)[CH3:62]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 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 11605551Bisindolylmaleimide XI hydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

185 mg of trifluoromethanesulfonic anhydride in 30 ml of dichloromethane were treated at 0° C. under a nitrogen atmosphere with a suspension of 140 mg of the pyrroledione product of Example 1 and 70 mg of collidine in 25 ml of dichloromethane. After 1.5 hour, 0.8 ml of a 33% solution of dimethylamine in ethanol was added and the mixture was stirred for 2.5 hours. The solvent was removed under reduced pressure and the residue was triturated with methanol to give a solid which was stirred with ethyl acetate saturated with hydrogen chloride. The solid was filtered off and dried to give 70 mg of 3-[6,7,8,9-tetrahydro-8-[(dimethylamino)methyl]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione hydrochloride of melting point 335°-336° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with methanol
  3. customto give a solid which
  4. filtrationThe solid was filtered off
  5. customdried

Sources & evidence

ORD record
ord-b83a4150614b49c2b63fd84dfa1d1110
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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