3-tert-butyl-1-phenyl-1H-pyrazol-5-amine → HCID 44133720、化合物

HRID 217867ノート

反応式

HRID 217867 の反応式
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]

参加物

5

反応物 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

生成物 1

HCID 44133720HCID 44133720、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-731975b3e712480689e05707bde82578
出典データセット
uspto-grants-2012_06
特許番号
US08198279B2

反応ノート

読み込み中…