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

HRID 2373885ノート

反応式

HRID 2373885 の反応式
[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

参加物

5

反応物 3

HCID 222Ammonia2 回HCID 18522661Acetone cardiceHCID 598527951-(3-Benzyloxyphenyl)-3-tert-butyl-8-chloroimidazo[1,5-a]pyrazine

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
110 °C

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-6700f06224014723ae35dc3aafb0a9da
出典データセット
uspto-grants-2008_12
特許番号
US07459554B2

反応ノート

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