Pyridine → HCID 14986916, compound

HRID 1493584Notes

Reaction equation

HRID 1493584 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.[Cl:44][CH2:45][CH2:46][CH2:47][S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl>[Cl:44][CH2:45][CH2:46][CH2:47][S:48]([NH: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)(=[O:50])=[O:49]

Participants

5

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chloride2×HCID 14986929HCID 14986929, compound

Product 1

HCID 14986916HCID 14986916, 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 (0.1 g, 1.2 mmole) in methylene chloride (15 ml) at 0° was added, dropwise, a solution of 3-chloropropanesulphonyl chloride (0.072 g, 0.4 mmole) in methylene chloride (1 ml). The resulting mixture was stirred at 0° for 2 hours, an additional portion of 3-chloropropanesulphonyl chloride (0.036 g, 0.2 mmole) was added and stirring was continued overnight at room temperature, the reaction mixture was quenched by the addition of aqueous citric acid, the organic phase separated and washed with water. After drying over magnesium sulphate, the organic phase was concentrated under reduced pressure and the resulting gum purified by flash chromatography on silica gel eluting with ethyl acetate to yield, after collection and evaporation of appropriate fractions, the desired product as a foam, m.p. 80°- 81° (0.24 g, 96%).

Workup

  1. stirringstirring
  2. waitwas continued overnight at room temperature
  3. customthe reaction mixture was quenched by the addition of aqueous citric acid
  4. customthe organic phase separated
  5. washwashed with water
  6. dry with materialAfter drying over magnesium sulphate
  7. concentrationthe organic phase was concentrated under reduced pressure
  8. customthe resulting gum purified by flash chromatography on silica gel eluting with ethyl acetate
  9. customto yield
  10. customafter collection and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-1e35c24c1e4f4173a3daee380b17b4a2
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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