Ammonia → 1-(3-Benzyloxyphenyl)-3-tert-butylimidazo[1,5-a]pyrazin-8-ylamine

HRID 2373885노트

반응식

HRID 2373885 반응식
[NH3:1].C(=O)=O.CC(C)=O.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:26]3[CH:31]=[CH:30][N:29]=[C:28](Cl)[C:27]=23)[CH:20]=[CH:21][CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(O)C>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH2:1])[C:27]=23)[CH:20]=[CH:21][CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 222Ammonia2회HCID 18522661Acetone cardiceHCID 598527951-(3-Benzyloxyphenyl)-3-tert-butyl-8-chloroimidazo[1,5-a]pyrazine

생성물 1

HCID 112802111-(3-Benzyloxyphenyl)-3-tert-butylimidazo[1,5-a]pyrazin-8-ylamine

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
110 °C

실험 절차

Gaseous NH3 is condensed into a cooled (dry ice/acetone) solution of 1-(3-benzyloxyphenyl)-3-tert-butyl-8-chloroimidazo[1,5-a]pyrazine (61.8 mg, 0.158 mmol) in iPrOH (2 mL) in a pressure tube until the volume is doubled, then the tube is sealed and heated to 110° C. (bath temp.) overnight. The seal has leaked during that time, LC indicates ≈50% conversion; therefore, ammonia is condensed in and the tube is heated as described before. The crude material is purified by preparative TLC (1000 μm silica gel layer, 20×20 cm plate), eluting once with 1% MeOH in CH2Cl2 and then three times with hexanes:EtOAc 3:1. One obtains the title compound as pale yellow solid, >95% pure by HPLC; 1H NMR (CDCl3, 400 MHz) δ 1.57 (s, 9H), 5.06 (brs, 2H), 5.14 (s, 2H), 6.99-7.04 (m, 2H), 7.22-7.26 (m, 2H), 7.31-7.42 (m, 4H), 7.44 (d, J=8.4 Hz, 2H), 7.46 (d, J=5.3 Hz, 1H). MS (ES+): m/z 373.1 (100) [MH+].

후처리

  1. customcondensed into
  2. customthe tube is sealed
  3. customcondensed in and the tube
  4. temperatureis heated
  5. customThe crude material is purified by preparative TLC (1000 μm silica gel layer, 20×20 cm plate)
  6. washeluting once with 1% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-6700f06224014723ae35dc3aafb0a9da
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459554B2

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