Hydrochloric Acid → 5-[4-(4-{2-[(E)-2-(-4-Trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-2H-tetrazole

HRID 750958Notes

Reaction equation

HRID 750958 reaction equation
[H-].[Na+].[N:3]1[NH:4][N:5]=[N:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([C:36]([F:39])([F:38])[F:37])=[O:35])=[CH:30][CH:29]=2)[O:24][CH:25]=1.Cl>CN(C)C=O.O>[F:39][C:36]([F:37])([F:38])[S:34]([C:31]1[CH:32]=[CH:33][C:28](/[CH:27]=[CH:26]/[C:23]2[O:24][CH:25]=[C:21]([CH2:20][O:18][C:15]3[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][C:7]4[N:6]=[N:5][NH:4][N:3]=4)=[CH:17][CH:16]=3)[N:22]=2)=[CH:29][CH:30]=1)=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 236145484-(4-2H-tetrazol-5-yl-butyl)-phenolHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

Product 1

HCID 112837445-[4-(4-{2-[(E)-2-(-4-Trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-2H-tetrazoleYield 16.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

47.5 mg (1.88 mmol) 95% sodium hydride were given at 0° C. to a solution of 200 mg (0.916 mmol) 4-(4-2H-tetrazol-5-yl-butyl)-phenol in 5.0 ml N,N-dimethylformamide and stirred for 15 min. 308 mg (0.916 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole were added and stirring continued at 25° C. for 2 h. The reaction mixture was neutralized with HCl, poured into water and the resulting precipitate washed with little methanol and diethyl ether. The obtained material (180 mg) was purified by chromatography on silica gel (dichloromethane/methanol 100:4) to give 80 mg of the title compound.

Workup

  1. stirringstirring
  2. waitcontinued at 25° C. for 2 h
  3. washthe resulting precipitate washed with little methanol and diethyl ether
  4. customThe obtained material (180 mg) was purified by chromatography on silica gel (dichloromethane/methanol 100:4)

Sources & evidence

ORD record
ord-e7d6dd7a7f854600968123bc1126d144
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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