Hydrazine hydrate (1:1) → HCID 178470662, compound

HRID 1822224Notes

Reaction equation

HRID 1822224 reaction equation
O[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[C:19](=O)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1.O.[NH2:35][NH2:36]>CN(C=O)C>[CH2:31]([O:30][C:28]([CH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C:19]2[C:3]3[C:4](=[O:18])[N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:6]4[N:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2]=3[NH:36][N:35]=2)=[CH:22][CH:23]=1)=[O:29])[CH3:32]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54676208HCID 54676208, compound

Product 1

HCID 178470662HCID 178470662, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxy-3-[1-oxo-2-(4-ethoxycarbonylmethylphenyl)ethyl]-1-phenyl-1,8-naphthyridin-2 (1H)-one (128 mg, 0.29 mmol, prepared in Synthetic Example 26) in DMF (3 ml) was added hydrazine monohydrate (80%, 34 μl, 0.87 mmol, 3.0 eq.), and the mixture was treated in the same manner as in Example 16 to give 3-(4-ethoxycarbonylmethylbenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (115 mg, 91%).

Workup

  1. additionthe mixture was treated in the same manner as in Example 16

Sources & evidence

ORD record
ord-44d71dddd06949b09c96c0f5d92ab3e8
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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