HCID 14851909, compound → HCID 14851920, compound

HRID 1032793Notes

Reaction equation

HRID 1032793 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]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[CH2:27]([N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][C:31]1=[O:40])[C:28]#[CH:29]>>[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:29]#[C:28][CH2:27][N:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33][CH2:32][C:31]3=[O:40])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1

Participants

3

Reactant 2

HCID 14851909HCID 14851909, compoundHCID 14894666HCID 14894666, compound

Product 1

HCID 14851920HCID 14851920, compound

Procedure

The title compound was prepared by coupling 6-(2-fluorophenyl)-1-(trifluoromethyl)-8-iodo-4H-[1,2,4]triazolo [4,3-a][1,4]benzodiazepine with 3,4-dihydro-1-(2-propynyl)-2(1H)-quinolinone under the conditions used in Example 37. The product was purified by chromatoqraphy over the 50-fold amount of silica gel using 5% (v/v) of ethanol in methylene chloride. The clean fractions were combined and evaporated and the residue was crystallized from ethyl acetate to yield colorless crystals of 1-{3-[6-(2-fluorophenyl)-1-(trifluoromethyl)-4H-[1,2,4]triazolo[4,3-a][4,1]benzodiazepin-8-yl]-2-propynyl}-3,4-dihydro-2(1H)-quinolinone with m.p. 193°-196°.

Workup

  1. customThe product was purified by chromatoqraphy over the 50-fold amount of silica gel using 5% (v/v) of ethanol in methylene chloride
  2. customevaporated
  3. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-576e9e54e20a4270b792c285e6e06fc6
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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