Hydrazine hydrate (1:1) → HCID 178514899, compound

HRID 1822215Notes

Reaction equation

HRID 1822215 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[S:22][CH:23]=[CH:24][CH:25]=1.O.[NH2:28][NH2:29]>CN(C=O)C>[S:22]1[CH:23]=[CH:24][CH:25]=[C:21]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:29][N:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54676204HCID 54676204, compound

Product 1

HCID 178514899HCID 178514899, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxy-3-[1-oxo-2-(2-thienyl)ethyl]-1-phenyl-1,8-naphthyridin-2 (1H)-one (30 mg, 0.08 mmol, prepared in Synthetic Example 17) in DMF (1.5 ml) was added hydrazine monohydrate (80%, 30 μl, 0.75 mmol, 9.4 eq.), and the mixture was treated in the same manner as in Example 16 to give 3-(2-thienylmethyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (22 mg, 72%).

Workup

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

Sources & evidence

ORD record
ord-004749d8c03e40f4bdf7ca6a3acc1958
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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