Hydrazine hydrate (1:1) → HCID 178514902, compound

HRID 217416Notes

Reaction equation

HRID 217416 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)[CH2:25][C:26]1[CH:30]=[CH:29][S:28][CH:27]=1.O.[NH2:33][NH2:34].C(=O)([O-])O.[Na+]>CN(C=O)C>[S:28]1[CH:29]=[CH:30][C:26]([CH2:25][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:20])([F:21])[F:22])[CH:13]=4)[C:6]4[N:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2]=3[NH:34][N:33]=2)=[CH:27]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 68948027HCID 68948027, compound

Product 1

HCID 178514902HCID 178514902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of 4-hydroxy-3-(3-thienylacetyl)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one (80 mg, 0.18 mmol) produced in Synthesis Example 42 in DMF (3 mL) was added hydrazine monohydrate (purity of 80%, 44 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. The resulting precipitate was separated by filtration, washed with water, recrystallized from methanol, and dried to give 3-(3-thienylmethyl)-5-(3-trifluoromethoxyphenyl)-1H-pyrazolo[4,3-c][1,8]-naphthyridin-4(5H)-one as a form of crystal (47 mg, yield 60%).

Workup

  1. customThe resulting precipitate was separated by filtration
  2. washwashed with water
  3. customrecrystallized from methanol
  4. customdried

Sources & evidence

ORD record
ord-dc2ce551fc0444eb8bfea71864c71ffc
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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