5-Amino-6,8-difluoro-2-[3-fluoro-4-[(3-phthalimidopropyl)amino]phenyl]-4H-1-benzopyran-4-one → 5-Amino-2-[4-(3-aminopropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736111Notes

Reaction equation

HRID 1736111 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:34])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][N:22]4C(=O)C5=CC=CC=C5C4=O)=[C:14]([F:33])[CH:13]=3)[O:11][C:6]=2[C:5]([F:35])=[CH:4][C:3]=1[F:36]>CN(C)C=O.CO.O.NN>[NH2:1][C:2]1[C:7]2[C:8](=[O:34])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][NH2:22])=[C:14]([F:33])[CH:13]=3)[O:11][C:6]=2[C:5]([F:35])=[CH:4][C:3]=1[F:36]

Participants

5

Reactant 1

HCID 153469955-Amino-6,8-difluoro-2-[3-fluoro-4-[(3-phthalimidopropyl)amino]phenyl]-4H-1-benzopyran-4-one

Product 1

HCID 194348055-Amino-2-[4-(3-aminopropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

800 mg of Compound 29 was dissolved in 100 ml of a mixed solvent of dimethylformamide and methanol (1:1), 0.787 ml of hydrazine monohydrate was added and the mixture was stirred at 50° to 60° C. for 1 hour. The reaction solution was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography (chloroform:methanol:aqueous ammonia=9:1:1) to give Compound 30 which was dissolved in ethanol, a 5.5N hydrochloric acid-isopropylalcohol solution was added, and the precipitated crystals were collected by filtration to give 321 mg (49%) of hydrochloride of Compound 30.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9134b7c9c5ad457e9287c05ef809ccc0
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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