Ethanol → 4-(2-Chloro-phenyl)-9-methyl-2-[3-(1,2,3,4-tetrahydro-carbazol-9-yl)-prop-1-ynyl]-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulene

HRID 1032782Notes

Reaction equation

HRID 1032782 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16](I)[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1.[CH2:23]([N:26]1[C:38]2[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:24]#[CH:25].C(O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:25]#[C:24][CH2:23][N:26]3[C:38]4[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=4[C:32]4[C:27]3=[CH:28][CH:29]=[CH:30][CH:31]=4)[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 127119101,2,3,4-tetrahydro-9-(2-propynyl)-9H-carbazoleHCID 148519244-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Product 1

HCID 148518914-(2-Chloro-phenyl)-9-methyl-2-[3-(1,2,3,4-tetrahydro-carbazol-9-yl)-prop-1-ynyl]-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was obtained by coupling 4-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine with 1,2,3,4-tetrahydro-9(2-propynyl)-9H-carbazole under the conditions used in Example 37. The product was isolated by chromatography over the 50-fold amount of silica gel using 8 % (v/v) of ethanol in methylene chloride for elution. The residue obtained after evaporation of the combined clean fractions containing product was crystallized from ethanol to give colorless crystals of 4-(2-chlorophenyl)-2-[3-(1,2,3,4-tetrahydro 9H-carbazol-9-yl)-1-propynyl]-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine with m.p. 164°-166°. These crystals contained 0.66 molar amounts of ethanol according to analytical and spectral data.

Workup

  1. customThe residue obtained
  2. customafter evaporation of the combined clean fractions
  3. additioncontaining product
  4. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-d723bd67263d4284b8b61dac047ab9b9
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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