1-Hydroxybenzotriazole → HCID 53241298, compound

HRID 1027585Notes

Reaction equation

HRID 1027585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[CH2:60]([N:67]1[CH2:71][CH2:70][CH:69]([CH2:72][NH2:73])[O:68]1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>C(#N)C.C(N(CC)CC)C>[CH2:60]([N:67]1[CH2:71][CH2:70][CH:69]([CH2:72][NH:73][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([C:11]3[CH2:10][C:9]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=4)([C:24]([F:27])([F:25])[F:26])[O:13][N:12]=3)=[CH:15][C:16]=2[CH3:23])[O:68]1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acidHCID 67246433HCID 67246433, compound

Product 1

HCID 53241298HCID 53241298, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (1.75 g) (prepared according to WO 2009/080250) in acetonitrile (35 ml) and triethylamine (2.04 ml) were added under nitrogen atmosphere TBTU (1.61 g), AZA.HOBT (0.68 g) and C-(2-Benzyl-isoxazolidin-5-yl)-methylamine (Step B, 1.61 g) were added. The resulting solution was stirred at room temperature for 4 hours, then quenched by addition of aqueous saturated ammonium chloride solution. The mixture was then extracted with ethyl acetate, dried over sodium sulfate, filtered then concentrated in vacuo. The residue purified by column chromatography (ethyl acetate/cyclohexane 1:1) to afford the title compound as a white solid (60 mg, (mixture of diasteroisomers). LCMS (Method F) 2.20 min, M+H 636/638.

Workup

  1. customquenched by addition of aqueous saturated ammonium chloride solution
  2. extractionThe mixture was then extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthen concentrated in vacuo
  6. customThe residue purified by column chromatography (ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-d98a7f04f5134df18a4da0f7db2ac514
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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