Water → HCID 67336132, compound

HRID 451531Notes

Reaction equation

HRID 451531 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([N:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)[CH2:8][CH2:9][CH2:10]O)=[N:5][N:6]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[F:19][C:14]1[CH:13]=[C:12]([N:7]2[CH2:8][CH2:9][CH2:10][N:5]3[N:6]=[C:2]([NH2:1])[N:3]=[C:4]23)[CH:17]=[CH:16][C:15]=1[F:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate2×HCID 178509195HCID 178509195, compound

Product 1

HCID 67336132HCID 67336132, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((5-amino-4H-1,2,4-triazol-3-yl)(3,4-difluorophenyl)amino)propan-1-ol (31 mg, 115 μmol) in tetrahydrofurane (1.15 mL) was added at 0° C. under an atmosphere of nitrogen triphenylphosphine (45.3 mg, 173 μmol). The reaction was stirred for 15 minutes and then DEAD (31.0 mg, 28.2 μL, 173 μmol) was added. The reaction was stirred for 30 minutes at 0° C. and then at room temperature over night. The same procedure was repeated with additional triphenylphosphine (45.3 mg, 173 μmol) and DEAD (31.0 mg, 28.2 μL, 173 μmol). Water was added and the reaction was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a colorless solid (14 mg, 48%) after column chromatography on silica gel using a gradient from methylene chloride to methylene chloride/methanol 19:1 (v/v) as eluent. MS ISP (m/e): 252.3 (100) [(M+H)+].

Workup

  1. stirringThe reaction was stirred for 30 minutes at 0° C.
  2. waitat room temperature over night
  3. extractionthe reaction was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59dbbab7c15b45078675cde5893760a1
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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