Ethanol → HCID 14851911, compound

HRID 1032789Notes

Reaction equation

HRID 1032789 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[C@H:10]([CH3:24])[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[C@H:10]([CH3:24])[N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14851913HCID 14851913, compoundHCID 14894666HCID 14894666, compound

Product 1

HCID 14851911HCID 14851911, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by coupling (S)-6-(2-fluorophenyl)-8-iodo-4,1-dimethyl-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 100. 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 crystallized very slowly from ethanol/ether to give colorless crystals of (S)-1-{3-[6-(2-fluorophenyl)-4,1-dimethyl4H-[1,2,4]-triazolo[4,3-a][4,1]benzodiazepin-8-yl]-2-propynyl}3,4-dihydro-2(1H)-quinolinone with m.p. 155°-160° with foaming. These crystals contained both ethanol and water according analytical and spectral data. [α]D=+87.5° (c=1.0091 in CH2Cl2)

Workup

  1. customThe combined clean fractions were evaporated
  2. customthe residue crystallized very slowly from ethanol/ether

Sources & evidence

ORD record
ord-569d0e72b9e5461eab378e2c9452b8a4
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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