Triphenylphosphine → HCID 136149941, compound

HRID 2263430Notes

Reaction equation

HRID 2263430 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:22][C:21](=[O:23])[O:20][N:19]=2)=[C:14]([F:24])[CH:13]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.O>[NH2:1][CH2:4][C:5]1[N:6]=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:27][CH:26]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:22][C:21](=[O:23])[O:20][N:19]=2)=[C:14]([F:24])[CH:13]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 136149990HCID 136149990, compound

Product 1

HCID 136149941HCID 136149941, compoundYield 4.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 118 mg of 3-{4-[4-azidomethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-fluoro-phenyl}-4H-1,2,4-oxadiazol-5-one in 0.25 mL of dimethylformamide and 0.022 mL of water was added 31 mg of triphenylphosphine. The resulting mixture was stirred for 20 h at room temperature and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from dichloromethane 100 to dichloromethane 90/methanol 10/water 1/acetic acid 1) followed by chromatography on a SCX Waters column with gradient CH2Cl2/MeOH 30/70 to 7N NH3 in MeOH to give 5.5 mg of 3-{4-[4-aminomethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-fluoro-phenyl}-4H-1,2,4-oxadiazol-5-one.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel (gradient from dichloromethane 100 to dichloromethane 90/methanol 10/water 1/acetic acid 1)

Sources & evidence

ORD record
ord-7b00dcd5a6e84f239af5828e89e44308
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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