Pyridine → HCID 14986915, compound

HRID 1493583Notes

Reaction equation

HRID 1493583 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:37]=[CH:36][C:17]([O:18][CH2:19][C:20]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=4[Cl:35])([OH:27])[CH2:21][N:22]4[CH:26]=[N:25][CH:24]=[N:23]4)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:44][C:45]([F:52])([F:51])[CH2:46][S:47](Cl)(=[O:49])=[O:48]>C(Cl)Cl>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[C:20]([OH:27])([CH2:19][O:18][C:17]1[CH:36]=[CH:37][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:47]([CH2:46][C:45]([F:52])([F:51])[F:44])(=[O:49])=[O:48])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1)[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 14986929HCID 14986929, compound

Product 1

HCID 14986915HCID 14986915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(4-[4-(4-aminophenyl)piperazin-1-yl]phenoxy)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (see Preparation 1) (0.2 g, 0.37 mmole) and pyridine (0.06 g, 0.75 mmole) in methylene chloride (20 ml) at 0° was added, dropwise, a solution of 2,2,2-trifluoroethanesulphonyl chloride (0.095 g, 0.52 mmole) in methylene chloride (1 ml) and the resulting mixture was stirred for 0.5 hour. The reaction was quenched by the addition of aqueous citric acid, the resulting organic phase separated, washed with water and dried over magnesium sulphate. After concentration under reduced pressure the residue was purified by flash chromatography on silica gel eluting with ethyl acetate (80):hexane (20) to yield, after collection and evaporation of appropriate fractions, the desired product as a foam, m.p. 74°-75° (0.159 g, 62%).

Workup

  1. customThe reaction was quenched by the addition of aqueous citric acid
  2. customthe resulting organic phase separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationAfter concentration under reduced pressure the residue
  6. customwas purified by flash chromatography on silica gel eluting with ethyl acetate (80)
  7. customhexane (20) to yield
  8. customafter collection and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-9521a6ddc7e84faf8a4ed89c7723ec51
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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