Ammonia → HCID 5327740, compound

HRID 863675Notes

Reaction equation

HRID 863675 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(O[CH2:20][CH:21]1[CH2:50][N:25]2[C:26]3[C:31]([C:32]([C:33]4[C:34](=[O:49])O[C:36](=[O:48])[C:37]=4[C:38]4[C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[N:40]([CH3:47])[CH:39]=4)=[C:24]2[CH2:23][CH2:22]1)=[CH:30][CH:29]=[CH:28][CH:27]=3)(=O)C.[N:51]1C(C)=CC(C)=CC=1C.[NH3:60]>ClCCl>[NH2:60][CH2:20][CH:21]1[CH2:50][N:25]2[C:26]3[C:31]([C:32]([C:33]4[C:34](=[O:49])[NH:51][C:36](=[O:48])[C:37]=4[C:38]4[C:46]5[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=5)[N:40]([CH3:47])[CH:39]=4)=[C:24]2[CH2:23][CH2:22]1)=[CH:30][CH:29]=[CH:28][CH:27]=3

Participants

6

Reactant 4

HCID 222AmmoniaHCID 79532,4,6-TrimethylpyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10096174HCID 10096174, compound

Product 1

HCID 5327740HCID 5327740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

200 mg of trifluoromethanesulfonic anhydride in 50 ml of dichloromethane were treated at 0° C. under a nitrogen atmosphere with a suspension of 150 mg of the pyrroledione product of Example 9 and 75 mg of collidine in 50 ml of dichloromethane. After 2 hours, 4 ml of 33% aqueous ammonia were added and the mixture was left to warm to room temperature overnight. The mixture was washed with water, dried and evaporated to dryness. The residue was purified by chromatography on silica gel with dichloromethane/methanol/acetone/water (90:18:3:2). Crystallization from dichloromethane/n-hexane gave 85 mg of 3-[7-(aminomethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 160°-165° C.

Workup

  1. waitthe mixture was left
  2. washThe mixture was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on silica gel with dichloromethane/methanol/acetone/water (90:18:3:2)
  6. customCrystallization from dichloromethane/n-hexane

Sources & evidence

ORD record
ord-2fd3228342014e298f177ca3c473632b
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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