Cyclopropanemethanamine → 1-(6-[(Cyclopropylmethyl)amino]pyrazin-2-yl]-1H-benzimidazol-6-amine

HRID 2192687ノート

反応式

HRID 2192687 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[N:4][CH:3]=1.[CH:18]1([CH2:21][NH2:22])[CH2:20][CH2:19]1.CCN(C(C)C)C(C)C>C(OC(O)C)C>[CH:18]1([CH2:21][NH:22][C:2]2[N:7]=[C:6]([N:8]3[C:12]4[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=4[N:10]=[CH:9]3)[CH:5]=[N:4][CH:3]=2)[CH2:20][CH2:19]1

参加物

5

反応物 3

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 582170941-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine

生成物 1

HCID 597839471-(6-[(Cyclopropylmethyl)amino]pyrazin-2-yl]-1H-benzimidazol-6-amine

試薬・触媒・溶媒 1

HCID 101298981-Ethoxyethanol溶媒

実験手順

A solution of 1-(6-chloropyrazin-2-yl)-1H-benzimidazol-6-amine (100 mg, 0.41 mmol) and cyclopropylmethylamine (424 μL, 4.1 mmol) in ethoxyethanol (2 mL) containing DIPEA (140 μL) was heated at reflux overnight under N2. The solution was concentrated under reduced pressure and the residue dissolved in EtOAc (20 mL) and washed successively with H2O (20 mL), 1M HCl (2×20 mL), H2O (20 mL) and brine (20 mL). After drying (Na2SO4) the solvent was removed under reduced pressure and the residue chromatographed eluting with dichloromethane-methanol (9:1-94:6) to separate pure product from the lower fractions (98 mg)

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight under N2
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue dissolved in EtOAc (20 mL)
  5. washwashed successively with H2O (20 mL), 1M HCl (2×20 mL), H2O (20 mL) and brine (20 mL)
  6. dry with materialAfter drying (Na2SO4) the solvent
  7. customwas removed under reduced pressure
  8. customthe residue chromatographed
  9. washeluting with dichloromethane-methanol (9:1-94:6)
  10. customto separate pure product from the lower fractions (98 mg)

出典と根拠

ORDレコード
ord-255747a51e3945df962dd3c11b5da6e9
出典データセット
uspto-grants-2012_12
特許番号
US08329737B2

反応ノート

読み込み中…