HCID 19434809, compound → HCID 19434871, compound

HRID 1736104Notes

Reaction equation

HRID 1736104 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][CH:3]=1>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][CH:3]=1

Participants

5

Reactant 1

HCID 19434809HCID 19434809, compound

Product 1

HCID 19434871HCID 19434871, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
55 °C

Procedure

4.22 g of Compound 19 was dissolved in 200 ml of a mixed solvent of dimethylformamide and methanol (1:1), 9.0 ml of hydrazine monohydrate was added and the mixture was stirred at 50-60° C. for 20 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 20 which was dissolved in ethanol, a 5.5N hydrochloric acid-isopropylalcohol solution was added, and the precipitated crystals were collected by filtration to give 1.47 g (40%) of Compound 20.

Workup

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

Sources & evidence

ORD record
ord-c3a919a6be234aa8bfd147220231ab12
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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