3-tert-butyl-1-phenyl-1H-pyrazol-5-amine → HCID 44133720, compound

HRID 1035456Notes

Reaction equation

HRID 1035456 reaction equation
C[Al](C)C.[C:5]([C:9]1[CH:13]=[C:12]([NH2:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)([CH3:8])([CH3:7])[CH3:6].[O:21]=[C:22]1[NH:27][C:26]2[N:28]=[CH:29][CH:30]=[C:31]([O:32][C:33]3[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=3)[C:36](OC)=[O:37])[C:25]=2[N:24]=[CH:23]1>C1COCC1>[C:5]([C:9]1[CH:13]=[C:12]([NH:14][C:36](=[O:37])[C:35]2[CH:40]=[CH:41][CH:42]=[C:33]([O:32][C:31]3[C:25]4[N:24]=[CH:23][C:22](=[O:21])[NH:27][C:26]=4[N:28]=[CH:29][CH:30]=3)[CH:34]=2)[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amineHCID 16682925TrimethylaluminumHCID 44134094Methyl 3-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)benzoate

Product 1

HCID 44133720HCID 44133720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Method H1: A solution of AlMe3 (solution in toluene 2M, 0.85 mL, 1.68 mmol,) was added dropwise to a cooled (0 C) solution of 3-tert-butyl-1-phenyl-1H-pyrazol-5-amine (362 mg, 1.68 mmol) in THF (5.0 mL). When the addition was complete, the mixture was allowed to warm to room temperature and stirring was continued for 30 minutes. Then methyl 3-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)benzoate (100 mg, 0.336 mmol) was added and the mixture was heated under reflux for 19 h. The mixture was cooled to room temperature and carefully quenched with 5% aq HCl (3.0 mL). After evaporation of solvent, the residue was retaken in CH2Cl2, washed with saturated solution of NaHCO3 and dried over MgSO4 and evaporated under vacuum. The obtained residue was chromatographied (eluent: CH2Cl2/EtOAc: 2/1 towards 1/3) and the title compound was obtained as a slightly yellow solid (29 mg, 18%).

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 19 h
  4. temperatureThe mixture was cooled to room temperature
  5. customcarefully quenched with 5% aq HCl (3.0 mL)
  6. customAfter evaporation of solvent
  7. washwashed with saturated solution of NaHCO3
  8. dry with materialdried over MgSO4
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-66eafb60a0a346a695bd788c9242f3ad
Source dataset
uspto-grants-2013_10
Patent number
US08546387B2

Reaction notes

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