Hydrazine hydrate (1:1) → HCID 178435925, compound

HRID 217406Notes

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

Participants

Conditions

Temperature: 115 °C

Procedure

To a suspension of 4-hydroxy-3-(2-phenylpropionyl)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one (276 mg, 0.61 mmol) produced in Synthesis Example 32 in DMF (3 mL) was added hydrazine monohydrate (purity of 80%, 100 μL), and the mixture was stirred at 110 to 120° C. for 2 hours. To the reaction solution was added a sodium hydrogencarbonate aqueous solution, and an oily substance was collected. To the oily substance was added isopropyl ether, and the mixture was heated. Then the resulting matter was allowed to stand to a room temperature for crystallization. The resulting crystal was separated by filtration and dried to give 3-(1-phenylethyl)-5-(3-trifluoromethoxyphenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4(5H)-one as a form of crystal (140 mg, yield 51%).

Workup

customan oily substance was collected
additionTo the oily substance was added isopropyl ether
temperaturethe mixture was heated
customto stand to a room temperature for crystallization
customThe resulting crystal was separated by filtration
customdried

Sources & evidence

ORD record: ord-bbb489b049ce4eebb4535c17a329327b
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193356B2

Reaction notes

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