3-tert-butyl-1-phenyl-1H-pyrazol-5-amine → N-(3-tert-butyl-1-phenylpyrazol-5-yl)-3-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-7-yl)oxy]benzamide

HRID 552444노트

반응식

HRID 552444 반응식
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:41][C:25]2=[N:26][CH:27]=[CH:28][C:29]([O:30][C:31]3[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=3)[C:34](OC)=[O:35])=[C:24]2[NH:23]1>C1COCC1>[C:5]([C:9]1[CH:13]=[C:12]([NH:14][C:34](=[O:35])[C:33]2[CH:38]=[CH:39][CH:40]=[C:31]([O:30][C:29]3[CH:28]=[CH:27][N:26]=[C:25]4[NH:41][C:22](=[O:21])[NH:23][C:24]=34)[CH:32]=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]

참가 물질

5

반응물 3

HCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amineHCID 16682925TrimethylaluminumHCID 45139752methyl 3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)benzoate

생성물 1

HCID 45139935N-(3-tert-butyl-1-phenylpyrazol-5-yl)-3-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-7-yl)oxy]benzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Method L2: A solution of AlMe3 (solution in toluene 2M, 260 μL, 0.527 mmol,) was added dropwise to a cooled (0° C.) solution of 3-tert-butyl-1-phenyl-1H-pyrazol-5-amine (113 mg, 0.527 mmol) in THF (2.5 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-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)benzoate (100 mg, 0.351 mmol) was added and the mixture was heated under reflux for 19 hours. The mixture was cooled to room temperature and carefully quenched with 5% aq HCl (1 mL). After evaporation of solvent, the residue was retaken in CH2Cl2, washed with saturated solution of NaHCO3 then with brine, dried over MgSO4 and evaporated under vacuum. The obtained residue was chromatographied (eluent: EtOAc) and the title compound was obtained as a light yellow solid (54 mg, 33%). 1H-NMR (δ, ppm, DMSO-d6): 1.30 (s, 9H, tBu), 6.39 (s, 1H, Hpyrrazole) 6.51 (d, 1H, HPy,5, J=5.9 Hz), 7.31 (t, 1H, Harom, J=7.4 Hz), 7.37 (dd, 1H, Harom, J=8.0 Hz, J=2.3 Hz), 7.41-7.44 (m, 2H, Harom), 7.49-7.51 (m, 2H, Harom), 7.55-7.62 (m, 2H, Harom), 7.71 (d, 1H, Harom, J=8.1 Hz), 7.82 (d, 1H, HPy,6, J=5.9 Hz), 10.34 (s, 1H, NHamide), 11.18 (s, 1H, NHurea), 11.42 (s, 1H, NHurea). LC-MS (m/z): 469 (M+H).

후처리

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

출처 및 근거

ORD 기록
ord-5fae4119172d484aa3a47b23a83b01b0
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951819B2

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