6,8-Difluoro-2-[3-fluoro-4-[(3-phthalimidopropyl)amino]phenyl]-5-hexylamino-4H-1-benzopyran-4-one → 2-[4-(3-Aminopropylamino)-3-fluorophenyl]-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([F:42])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]4C(=O)C5=CC=CC=C5C4=O)=[C:13]([F:32])[CH:12]=3)=[CH:8][C:7](=[O:33])[C:6]=2[C:34]=1[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C)C=O.CO.O.NN>[NH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:5]3[C:4]([F:42])=[CH:3][C:2]([F:1])=[C:34]([NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:6]=3[C:7](=[O:33])[CH:8]=2)=[CH:12][C:13]=1[F:32]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
60 mg of Compound 32 was dissolved in 30 ml of a mixed solvent of dimethylformamide and methanol, 0.050 ml of hydrazine monohydrate was added and the mixture was stirred at 60° to 70° C. for 4.3 hours. The reaction solution was concentrated under reduced pressure, and the residue was subjected to preparative thin layer chromatography (chloroform:methanol:aqueous ammonia=9:1:1) to give Compound 33 which was dissolved in chloroform. A 5.5N hydrochloric acid-isopropylalcohol solution was added, the solvent was distilled off under reduced pressure and the residue was treated with isopropyl ether to form the slurry from which 33.6 mg (67%) of hydrochloride of Compound 33 was obtained.
Workup
- additionwas added
- concentrationThe reaction solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bf567000fcb940afbfcb38f5409f7bf6
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05539112
Reaction notes
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