Water → HCID 19434881, compound

HRID 1736194Notes

Reaction equation

HRID 1736194 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[CH:23][C:22]([F:26])=[C:21]([NH:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:32])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[CH:23][C:22]([F:26])=[C:21]([NH:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:32]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 19434913HCID 19434913, compound

Product 1

HCID 19434881HCID 19434881, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

438 mg (0.984 mmol) of the above 2-[4-(3-azidopropylamino)-3-fluorophenyl]-5-butylamino-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 25 mL of tetrahydrofuran, 389 mg (1.48mmol) of triphenylphosphine was added under ice-cooling and the mixture was stirred at room temperature for 1 hour. 25 mL of water was added thereto and the mixture was further stirred for 5.5 hours. The mixture was extracted twice with ethyl acetate, and the organic layer was washed once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=9:1:1) to give 380 mg of Compound 126 (yield: 92%), which was converted to hydrochloride according to the conventional method.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 5.5 hours
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. washthe organic layer was washed once with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=9:1:1)

Sources & evidence

ORD record
ord-d3267a4056cc45f0bd6ec0c4207abe93
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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