Ethanol → HCID 14851922, compound

HRID 1032795Notes

Reaction equation

HRID 1032795 reaction equation
[F: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)[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([O:24][CH3:25])[N:9]=1.[CH2:26]([N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][C:30]1=[O:39])[C:27]#[CH:28].C(O)C>C(Cl)Cl>[F: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:28]#[C:27][CH2:26][N:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:32][CH2:31][C:30]3=[O:39])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([O:24][CH3:25])[N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14851919HCID 14851919, compoundHCID 14894666HCID 14894666, compound

Product 1

HCID 14851922HCID 14851922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by coupling rac-6-(2-fluorophenyl)-8-iodo-4-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepine with 3,4-dihydro-1-(2-propynyl)-2(1H)-quinolinone under the conditions used in Example 37. 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-1-{3-[6-(2-fluorophenyl)-4-methoxy-1-methyl-4H[1,2,4]triazolo[4,3-a][1,4] benzodiazepin-8-yl]-2-propynyl}-3,4-dihydro-2(1H)-quinolinone with m.p. 155°-160°. These crystals contained 0.33 molar equivalents of water.

Workup

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

Sources & evidence

ORD record
ord-6f8fc9c0196d41ab8f8109a9afc58725
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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