1-Hydroxybenzotriazole → HCID 66618761, compound

HRID 406306Notes

Reaction equation

HRID 406306 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:10]=[C:11]([CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:15][CH2:16][C:17](O)=[O:18])[NH:12][N:13]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1.C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>O1CCCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:10]=[C:11]3[CH:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:28])([F:29])[F:27])[CH2:15][CH2:16][C:17](=[O:18])[N:12]3[N:13]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 66778435HCID 66778435, compound

Product 1

HCID 66618761HCID 66618761, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[5-[6-Methoxy-5-(4-methyl-imidazol-1-yl)-pyridin-2-yl]-2H-[1,2,4]-triazol-3-yl]-4-(2-trifluoromethylphenyl)-butyric acid (208 mg) was dissolved in tetrahydrofuran (4.3 ml). Diisopropylethylamine (220 ul), 1-hydroxybenzotriazole (86.8 mg) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (334 mg) were added at room temperature and the reaction was initiated. After 19 hours, the reaction was terminated with water, followed by dilution with ethyl acetate. The organic layer was washed with saturated ammonium chloride and brine and dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 100%) to obtain the title compound (128 mg) as an orange solid.

Workup

  1. customthe reaction was terminated with water
  2. washThe organic layer was washed with saturated ammonium chloride and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave an oil
  6. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 100%)

Sources & evidence

ORD record
ord-cc3c24d0ecf544518f774b325cb3568c
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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