Methanol → HCID 136014640, compound

HRID 1172695Notes

Reaction equation

HRID 1172695 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]([C:13]2[S:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:15][C:14]=2[CH3:28])[CH2:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C:29]1[NH:33][C:32](=[O:34])[O:31][N:30]=1.B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]([C:13]2[S:17][C:16]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=3)=[N:15][C:14]=2[CH3:28])[CH2:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C:29]1[NH:33][C:32](=[O:34])[O:31][N:30]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 136014633HCID 136014633, compound

Product 1

HCID 136014640HCID 136014640, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 136 mg of 3-(2-methoxy-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-4H-1,2,4-oxadiazol-5-one in 5 mL of dichloromethane at −70° C. was added 0.6 mL of a 1 M solution of boron tribromide in dichloromethane. After 1 h at −60° C., the reaction mixture was poured into methanol and a saturated aqueous solution of NaHCO3 then extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10) to give 22 mg of 3-(2-hydroxy-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-4H-1,2,4-oxadiazol-5-one.

Workup

  1. extractiona saturated aqueous solution of NaHCO3 then extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-25fd098bd97046d1a99762063dcacb26
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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