Hydrazine hydrate (1:1) → HCID 178435924, compound

HRID 217412Notes

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]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:4](=[O:22])[C:3]=1[C:23](=O)[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:25].O.[NH2:34][NH2:35].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:26]1([CH:24]([C:23]2[C:3]3[C:4](=[O:22])[N:5]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[CH:13]=4)[C:6]4[N:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2]=3[NH:35][N:34]=2)[CH3:25])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 115 °C

Procedure

To a suspension of 4-hydroxy-3-(2-phenylpropionyl)-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one (119 mg, 0.27 mmol) produced in Synthesis Example 38 in DMF (1 mL) was added hydrazine monohydrate (purity of 80%, 43 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-trifluoromethylphenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4(5H)-one as a form of crystal (69 mg, yield 59%).

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-86db63eda30340dd98bd36b06183fd29
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193356B2

Reaction notes

Loading…