Hydrazine hydrate (1:1) → HCID 178490031, compound

HRID 1822212Notes

Reaction equation

HRID 1822212 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][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1.O.[NH2:31][NH2:32]>CN(C=O)C>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:19]1[C:3]2[C:4](=[O:18])[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:32][N:31]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54676176HCID 54676176, compound

Product 1

HCID 178490031HCID 178490031, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxy-3-[1-oxo-2-(3-methoxyphenyl)ethyl]-1-phenyl-1,8-naphthyridin-2 (1H)-one (50 mg, 0.13 mmol, prepared in Synthetic Example 14) in DMF (1 ml) was added hydrazine monohydrate (80%, 20 μl, 0.50 mmol, 3.8 eq.), and the mixture was treated in the same manner as in Example 16 to give 3-(3-methoxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (41 mg, 83%).

Workup

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

Sources & evidence

ORD record
ord-474d6748ee074e62b1bf93b90772760c
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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