Ethanol → HCID 131716590, compound

HRID 1032771Notes

Reaction equation

HRID 1032771 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]([C:26]12[CH2:37][CH2:36][CH2:35][C:33]3[C:34]1=[C:29]([CH:30]=[CH:31][CH:32]=3)[NH:28]C2=O)[C:24]#C.[CH2:39]([OH:41])[CH3:40]>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:24]#[C:23][CH2:26][CH:37]3[CH:40]4[C:39](=[O:41])[NH:28][C:29]5[CH:30]=[CH:31][CH:32]=[C:33]([C:34]=54)[CH2:35][CH2:36]3)[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 14851948HCID 14851948, compound

Product 1

HCID 131716590HCID 131716590, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared 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 rac-2a,3,4,5-tetrahydro-2a-(2-propynyl)benz[cd]indol-2(1H)-one under the conditions described in Example 17. The product was isolated by chromatography over the 50-fold amount of silica gel using 5% (v/v) of ethanol in methylene chloride for elution. The combined clean fractions were evaporated and the residue was crystallized from ethyl acetate/ether to give colorless crystals of rac-2a-{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}-2a,3,4,5-tetrahydrobenz[cd]indol-2(1H) one with m.p. 215°-217°.

Workup

  1. customThe combined clean fractions were evaporated
  2. customthe residue was crystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-4898905090124ee4a6379d60ca17b289
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

Loading…