Dimethylformamide → HCID 10029328, compound

HRID 863689Notes

Reaction equation

HRID 863689 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:38][N:13]2[C:14]3[C:19]([C:20]([C:21]4[C:22](=O)[O:23][C:24](=[O:36])[C:25]=4[C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]([CH3:35])[CH:27]=4)=[C:12]2[CH2:11][CH2:10]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:40](C)C=O>N>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:38][N:13]2[C:14]3[C:19]([C:20]([C:21]4[C:22](=[O:23])[NH:40][C:24](=[O:36])[C:25]=4[C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]([CH3:35])[CH:27]=4)=[C:12]2[CH2:11][CH2:10]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 10097892HCID 10097892, compound

Product 1

HCID 10029328HCID 10029328, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 85 mg of 3-[7-t-butoxyformamido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 5 ml of dimethylformamide and 5 ml of 33% aqueous ammonia was heated to 100° C. for 1 hour. The cooled mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried and evaporated. Crystallization from ethyl acetate/n-hexane gave 70 mg of 3-[7-t-butoxyformamido-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 159°-163° C.

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated
  5. customCrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-85d34ffe966647b4bd3fab5658c553d2
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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