Ethanol → HCID 14851921, compound

HRID 1032794Notes

Reaction equation

HRID 1032794 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]([OH:24])[N:9]=1.[CH2:25]([N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][C:29]1=[O:38])[C:26]#[CH:27].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:27]#[C:26][CH2:25][N:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:31][CH2:30][C:29]3=[O:38])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([OH:24])[N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14851918HCID 14851918, compoundHCID 14894666HCID 14894666, compound

Product 1

HCID 14851921HCID 14851921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was obtained by reacting rac-6-(2-fluorophenyl)-4-hydroxy-8-iodo-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. The combined good fractions were evaporated and the residue was crystallized from methanol/ethyl acetate to give colorless crystals of rac-1-{3-[6-(2-fluorophenyl)-4-hydroxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepin-8-yl]-2-propynyl}-3,4-dihydro-2(1H)-quinolinone with m.p. 253°-255° with decomposition. These crystals contained molar equivalents of water.

Workup

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

Sources & evidence

ORD record
ord-b9e57996449a4965b0ae3a6782a1f32b
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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