Ammonia → HCID 9903787, compound

HRID 1792831Notes

Reaction equation

HRID 1792831 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[N:7]=1)=O)C.[NH3:24]>CO>[O:17]([C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH:9]=[CH:10][C:6]([C:4]([NH2:24])=[O:3])=[N:7]2)=[CH:12][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22025365HCID 22025365, compound

Product 1

HCID 9903787HCID 9903787, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-ethoxycarbonyl-1-(4-phenoxyphenyl)-1H-pyrazole (120 mg, 0.39 mmol) in 5 mL of a 2N solution of ammonia in MeOH was stirred at rt for 4 d. TLC showed incomplete reaction and the solution was transferred to a sealed tube and heated at 70° C. overnight. The reaction was concentrated and purified by preparative TLC, eluting with 50% EtOAc/hexane, to yield 1-(4-phenoxyphenyl)-1H-pyrazole-3-carboxamide (Rf=0.26, 56 mg, 52%), mp 165-167° C. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (d, J=2.7 Hz, 1H, pyrazole), 7.92 (d, J=9.0 Hz, 2H, Phenyl), 7.71 (br, 1H, NH2), 7.43 (m, 2H, Phenoxy), 7.39 (br, 1H, NH2), 7.18 (m, 1H, Phenoxy), 7.17 (d, J 9.0 Hz, 2H, Phenyl), 7.07 (m, 2H, Phenoxy), 6.87 (d, J=2.7 Hz, 1H, pyrazole).

Workup

  1. customreaction
  2. customthe solution was transferred to a sealed tube
  3. concentrationThe reaction was concentrated
  4. custompurified by preparative TLC
  5. washeluting with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-47043342eedf41c39c183b9b9d91e68b
Source dataset
uspto-grants-2006_07
Patent number
US07078426B2

Reaction notes

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