3-Amino-5-phenylpyrazole → HCID 66719137, compound

HRID 2362183Notes

Reaction equation

HRID 2362183 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20]N(C)C)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:32]1([C:38]2[CH:39]=[C:40]([NH2:43])[NH:41][N:42]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)(=O)C.C(O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][N:41]4[N:42]=[C:38]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:39]=[C:40]4[N:43]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 1366553-Amino-5-phenylpyrazoleHCID 66719111HCID 66719111, compound

Product 1

HCID 66719137HCID 66719137, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 (250 mg, 0.59 mmol) and 5-Phenyl-2H-pyrazol-3-ylamine (96 mg, 0.59 mmol) in acetic acid (0.4 mL) and ethanol (1.6 mL) was heated under reflux for 6 hours. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with NaHCO3 aq. and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 9-1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. washthe combined organic phase was washed with NaHCO3 aq. and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep.TLC
  8. customto give 9-1

Sources & evidence

ORD record
ord-fd38c85b59da4b9a91d6f847b4f78927
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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