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

HRID 2192687노트

반응식

HRID 2192687 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 101298981-Ethoxyethanol용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-255747a51e3945df962dd3c11b5da6e9
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329737B2

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