HCID 15346993, compound → HCID 19434999, compound

HRID 1736106Notes

Reaction equation

HRID 1736106 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:33])[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)=[CH:14][CH:13]=3)[O:11][C:6]=2[C:5]([F:34])=[CH:4][C:3]=1[F:35]>CN(C)C=O.CO.O.NN>[NH2:1][C:2]1[C:7]2[C:8](=[O:33])[CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([NH:18][CH2:19][CH2:20][CH2:21][NH2:22])=[CH:16][CH:17]=3)[O:11][C:6]=2[C:5]([F:34])=[CH:4][C:3]=1[F:35]

Participants

5

Reactant 1

HCID 15346993HCID 15346993, compound

Product 1

HCID 19434999HCID 19434999, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 24654Hydrazine hydrate (1:1)Solvent2×

Procedure

600 mg of Compound 23 was dissolved in 75 ml of a mixed solvent of dimethylformamide and methanol (1:1), 0.613 ml of hydrazine monohydrate was added and the mixture was stirred at 50° to 60° C. for 1.5 hours. Additional 0.307 ml of hydrazine monohydrate was added and the mixture was stirred at 50° to 60° C. for 10 minutes. 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 24 which was dissolved in ethanol, a 5.5N hydrochloric acid-isopropylalcohol solution was added, and the precipitated crystals were collected by filtration to give 331 mg (69%) of Compound 24.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 50° to 60° C. for 10 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-82d0281133c74fb188c11e9dc22c7013
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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