Pyridine → HCID 19977040, compound

HRID 1450521Notes

Reaction equation

HRID 1450521 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[N:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[NH2:31])[N:23]=2)=[CH:15][CH:14]=1)(=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].N1C=CC=CC=1>ClCCl>[C:6]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[N:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[NH:31][S:2]([CH3:1])(=[O:4])=[O:3])[N:23]=2)=[CH:17][CH:18]=1)(=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19977054HCID 19977054, compound

Product 1

HCID 19977040HCID 19977040, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (114.5 mg) was added to a solution of 4-[2-(2-aminobenzyl)tetrazol-5-yl]phenyl pivalate (0.351 g), obtained in example 78, and pyridine (79 mg) in dichloromethane (2 ml) under ice cooling, and stirring was continued for 15 h. The mixture was washed with water, dried and evaporated to dryness. The residue was purified by column chromatography on silica gel with ethyl acetate-hexane (1/2) as an eluate. Recrystallization from ethyl acetate-hexane gave 300 mg (70%) of the title compound.

Workup

  1. washThe mixture was washed with water
  2. customdried
  3. customevaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel with ethyl acetate-hexane (1/2) as an eluate
  5. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-538fe5d89b6d45aaa649f1121033f478
Source dataset
uspto-grants-1997_02
Patent number
US05602161

Reaction notes

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