Water → 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol

HRID 221867노트

반응식

HRID 221867 반응식
Cl.[C:2]([C:6]1[CH:7]=[C:8]([NH2:19])[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[N:10]=1)([CH3:5])([CH3:4])[CH3:3].Cl.[NH+]1C=CC=CC=1.O>CCOC(C)=O>[NH2:19][C:8]1[N:9]([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[N:10]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 21584435Pyridinium hydrochlorideHCID 670222745-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride

생성물 1

HCID 595579663-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol수율 19%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
195 °C

실험 절차

In a 500 mL round bottom flask was added 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride (8.42 g, 30 mmol) and pyridinium hydrochloride (13.8 g, 120 mmol). The reaction mixture was heated neat at 195° C. with stirring for 3 h. The mixture was cooled to room temperature, water (300 mL) and EtOAc (300 mL) were added, and then the organic phase was washed with saturated aq NaHCO3 and brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was purified by MPLC (80:20 hexane/EtOAc) to give the product 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenol (1.3 g, 19%). 1H-NMR (DMSO-d6) δ 7.20 (t, 1H), 7.00 (m, 2H), 6.50 (d, 1H), 5.30 (s, 1H), 5.10 (bs, 2H), 1.30 (s, 9H); MS LC-MS [M+H]+=232.2, RT=0.57 min.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washthe organic phase was washed with saturated aq NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by MPLC (80:20 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-28fb7d9993e1430b91707776875de31c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207166B2

반응 노트

불러오는 중…