3-Amino-5-phenylpyrazole → HCID 66718968, compound

HRID 2362187Notes

Reaction equation

HRID 2362187 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:14]2[CH:19]=[CH:18][C:17]([C:20](=O)[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22]N(C)C)=[CH:16][CH:15]=2)[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:34]1([C:40]2[CH:41]=[C:42]([NH2:45])[NH:43][N:44]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)(=O)C.C(O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:22][N:43]4[N:44]=[C:40]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[CH:41]=[C:42]4[N:45]=3)=[CH:18][CH:19]=2)[CH2:9][C:10]([OH:13])([CH3:12])[CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 1366553-Amino-5-phenylpyrazoleHCID 66823376HCID 66823376, compound

Product 1

HCID 66718968HCID 66718968, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2 (450 mg, 1 mmol) and 5-Phenyl-2H-pyrazol-3-ylamine (160 mg, 1 mmol) in acetic acid (2 mL) and ethanol (4 mL) was heated under reflux for 4 hours. After cooling, the mixture was diluted with 30 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 flash chromoatography to give 10-1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 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 flash chromoatography
  8. customto give 10-1

Sources & evidence

ORD record
ord-71f4cab55b2845599d9814e3b897022a
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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