Ethanol → HCID 14851873, compound

HRID 1032769Notes

Reaction equation

HRID 1032769 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:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]1=[O:36])[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:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=[CH:28][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

5

Reactant 3

HCID 702EthanolHCID 148519244-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepineHCID 14894684HCID 14894684, compound

Product 1

HCID 14851873HCID 14851873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by reacting 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-propynyl)-2(1H)quinolinone [ref. A. Lindquist et al., Acta Pharm. Suecica, 9,99 (1972)]as described in EXAMPLE 37. It was isolated by chromatography over 50 g of silica gel using 5% (v/v) of ethanol in methylene chloride and was further purified by rechromatography over 50 g of silica gel using tetrahydrofuran. Crystallization from ethyl acetate/methanol gave off-white crystals of 1-{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}-2(1H)-quinolinone with m.p. 162-165°. These crystals contained according to analytical data 0.5 molar amounts of water.

Workup

  1. customwas further purified by rechromatography over 50 g of silica gel
  2. customCrystallization from ethyl acetate/methanol

Sources & evidence

ORD record
ord-f2037cebe9f7441e824ef8970e41aefb
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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