Dibutylamine → 4-(2-chlorophenyl)-2-ethyl-6-(2-indolecarboxamido)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

HRID 981461Notes

Reaction equation

HRID 981461 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[CH:16]=[C:17]([CH2:19][CH3:20])[S:18][C:5]=2[N:4]2[C:21]([CH3:24])=[N:22][N:23]=[C:3]12.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[C:34](O)=[O:35].[I-].ClC1C=CC=C[N+]=1C.C(NCCCC)CCC>O1CCCC1>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:6]2[CH:16]=[C:17]([CH2:19][CH3:20])[S:18][C:5]=2[N:4]2[C:21]([CH3:24])=[N:22][N:23]=[C:3]2[CH:2]([NH:1][C:34]([C:26]2[NH:25][C:33]3[C:28]([CH:27]=2)=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:35])[N:8]=1

Participants

6

Reactant 4

HCID 8148DibutylamineHCID 72899Indole-2-carboxylic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 156622376-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Product 1

HCID 156622384-(2-chlorophenyl)-2-ethyl-6-(2-indolecarboxamido)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepineYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 120 ml of tetrahydrofuran were added 5.0 g of 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine, 2.7 g of indole-2-carboxylic acid, 4.3 g of 2-chloro-N-methyl pyridinium iodide and 6.2 g of dibutyl amine, and the mixture was heated under reflux while stirring for 90 minutes. After the solvent was distilled off under reduced pressure, the residue was washed with diisopropyl ether. Ethanol was added to separate crystals, which were collected by filtration. The thus-obtained crystals were recrystallized from chloroform-ethanol to give 4.9 g of 4-(2-chlorophenyl)-2-ethyl-6-(2-indolecarboxamido)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine, m.p. 284°-286° C. (decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. washthe residue was washed with diisopropyl ether
  5. additionEthanol was added
  6. customto separate crystals, which
  7. filtrationwere collected by filtration
  8. customThe thus-obtained crystals were recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-ed695dd57e9f4192945e35507bffeeaf
Source dataset
uspto-grants-1991_02
Patent number
US04992437

Reaction notes

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