Acetic Acid → HCID 178514067, compound

HRID 1822241Notes

Reaction equation

HRID 1822241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[C:14]2[C:15](=[O:29])[N:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[N:18]=[CH:19][CH:20]=[CH:21][C:22]=3[C:13]=2[NH:12][N:11]=1.C(O)(=O)C.[O-:34][C:35]#[N:36].[K+]>O>[C:23]1([N:16]2[C:17]3[N:18]=[CH:19][CH:20]=[CH:21][C:22]=3[C:13]3[NH:12][N:11]=[C:10]([CH2:9][CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[NH:1][C:35]([NH2:36])=[O:34])[C:14]=3[C:15]2=[O:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 178507493HCID 178507493, compound

Product 1

HCID 178514067HCID 178514067, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of 3-[2-(2-aminophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (38 mg, 0.09 mmol, prepared in Example 36) in a mixture solvent of acetic acid (1 mL) and water (1 mL) was added potassium cyanate (12 mg, 0.15 mmol, 1.7 eq) at room temperature. The mixture was stirred overnight at 35° C., and filtered to give precipitates which were washed with water and then dried to afford 5-phenyl-3-[2-(2-ureidophenyl)ethyl]-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (40 mg, 94%).

Workup

  1. filtrationfiltered
  2. customto give
  3. customprecipitates which
  4. washwere washed with water
  5. customdried

Sources & evidence

ORD record
ord-b39c6090d2eb4b0b937d988ef345b1bc
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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