Dimethylformamide → HCID 178489437, compound

HRID 1822214Notes

Reaction equation

HRID 1822214 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]=[CH:23][C:22]=1OC.[OH2:30].[NH2:31][NH2:32].[CH3:33]N(C=O)C>>[CH3:33][O:30][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][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:32][N:31]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 54676196HCID 54676196, compound

Product 1

HCID 178489437HCID 178489437, compoundYield 93%

Procedure

To a suspension of 4-hydroxy-3-[1-oxo-2-(2-methoxyphenyl)ethyl]-1-phenyl-1,8-naphthyridin-2 (1H)-one (121 mg, 0.31 mmol, prepared in Synthetic Example 16) in DMF (3 ml) was added hydrazine monohydrate (80%, 50 μl, 1.25 mmol, 4.0 eq.), and the mixture was treated in the same manner as in Example 16 to give 3-(2-methoxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (111 mg, 93%).

Workup

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

Sources & evidence

ORD record
ord-bb234014bbe24e319a434da0181af735
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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