4-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine → 2-{3-[4-(2-Chloro-phenyl)-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-2-yl]-prop-2-ynyl}-3,4-dihydro-2H-isoquinolin-1-one

HRID 1032780Notes

Reaction equation

HRID 1032780 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[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36])[C:24]#[CH:25]>O1CCCC1.CCCCCC>[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[CH2:35][CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]3=[O:36])[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

4

Reactant 2

HCID 148519244-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepineHCID 148519532-(Prop-2-yn-1-yl)isoquinolin-1(2H)-one

Product 1

HCID 148518892-{3-[4-(2-Chloro-phenyl)-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-2-yl]-prop-2-ynyl}-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

The title compound was synthesized 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 3,4-dihydro-2.(2-propynyl)1(2H)-isoquinolinone [ref. W. Schneider et al. Arch. pharm., 291, 560 (1958)]under the conditions described in EXAMPLE 37. The product was isolated by chromatography over the 50-fold amount of solica gel using tetrahydrofuran/hexane 4:1 for elution. The clean fractions were combined and evaporated and the residue was crystallized from ethyl acetate to give colorless crystals of 2-{3-[4-(2-chlorophenyl) 9 methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2.yl]-2-propynyl}-3,4-dihydro-1(2H)-isoquinolinone with m.p. 164°-166°.

Workup

  1. customThe product was isolated by chromatography over the 50-fold amount of solica gel
  2. washfor elution
  3. customevaporated
  4. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-671dc01ec7bf418b9f4a2ed8402b190f
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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