Ethanol → HCID 14851916, compound

HRID 1032790Notes

Reaction equation

HRID 1032790 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[CH2:10][N:9]=1.[C:24]([C:26]1([CH3:40])[CH2:31][CH2:30][C:29]2[C:32]([CH3:39])=[C:33]([OH:38])[C:34]([CH3:37])=[C:35]([CH3:36])[C:28]=2[O:27]1)#[CH:25].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:25]#[C:24][C:26]3([CH3:40])[CH2:31][CH2:30][C:29]4[C:32]([CH3:39])=[C:33]([OH:38])[C:34]([CH3:37])=[C:35]([CH3:36])[C:28]=4[O:27]3)[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6olHCID 14851835HCID 14851835, compound

Product 1

HCID 14851916HCID 14851916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by coupling 6-(2-fluoro-phenyl)-8-iodo-1-methyl-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepine with rac-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol [ref. H. Mayer et al., Helv. Chim. Acta, 67, 650 (1963)]under the conditions described 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 clean fractions containing product were combined and evaporated. The residue was crystallized from ethanol/ethyl acetate to give colorless crystals of rac-2-{[6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepin-8-yl]ethynyl}-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with m.p. 265°-267°.

Workup

  1. additionThe clean fractions containing product
  2. customevaporated
  3. customThe residue was crystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-a1a063cf349242828f275bec1219ea01
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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