HCID 19696341, compound → HCID 5327739, compound

HRID 863681Notes

Reaction equation

HRID 863681 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]1[CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][CH:6]1[CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

4

Reactant 1

HCID 19696341HCID 19696341, compound

Product 1

HCID 5327739HCID 5327739, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

200 mg of the pyrroledione product of Example 16 in 70 ml of methanol containing 40 mg of 10% Pd/C were shaken under a hydrogen atmosphere at a pressure of 3 atmospheres for 48 hours. The supernatant was decanted and evaporated. The residue was treated with 50 ml of a saturated solution of hydrogen chloride in ethyl acetate and was then purified by chromatography on silica gel with dichloromethane/methanol/acetic acid/water (60:18:2:3). Crystallization from ethyl acetate gave 20 mg of 3-[8-(2-aminoethyl)-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. customThe supernatant was decanted
  2. customevaporated
  3. additionThe residue was treated with 50 ml of a saturated solution of hydrogen chloride in ethyl acetate
  4. customwas then purified by chromatography on silica gel with dichloromethane/methanol/acetic acid/water (60:18:2:3)
  5. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a46a24b5da7e49968efb4c6d4dae2c80
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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