Ethanol → HCID 14851917, compound

HRID 1032791Notes

Reaction equation

HRID 1032791 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.[C:23]([C:25]1([CH3:39])[CH2:30][CH2:29][C:28]2[C:31]([CH3:38])=[C:32]([OH:37])[C:33]([CH3:36])=[C:34]([CH3:35])[C:27]=2[O:26]1)#[CH:24].C(O)C>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][C:25]3([CH3:39])[CH2:30][CH2:29][C:28]4[C:31]([CH3:38])=[C:32]([OH:37])[C:33]([CH3:36])=[C:34]([CH3:35])[C:27]=4[O:26]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 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6olHCID 148519244-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Product 1

HCID 14851917HCID 14851917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was obtained by coupling 4-(2-chlorophenyl)-2-iodo-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepine with rac-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol 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 combined clean fractions were evaporated and the residue was crystallized from ethyl acetate to give colorless crystals of rac-2-{[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]ethynyl}-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with m.p. 155°-160° with foaming. These crystals contained 1.5 molar amounts of water on the basis of the analytical and spectral data.

Workup

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

Sources & evidence

ORD record
ord-24ba48c3b7e54c03a2b73d212b0c0b0c
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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