2,6-Dichloropyrazine → N-(4-(6-Chloropyrazin-2-yloxy)naphthalen-1-yl)acetamide

HRID 16278

반응식

HRID 16278 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19](Cl)[N:18]=1>>[Cl:16][C:17]1[N:18]=[C:19]([O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=2)[CH:20]=[N:21][CH:22]=1

참가 물질

3

반응물 2

HCID 785042,6-DichloropyrazineHCID 235848N-(4-hydroxynaphthalen-1-yl)acetamide

생성물 1

HCID 59343458N-(4-(6-Chloropyrazin-2-yloxy)naphthalen-1-yl)acetamide수율 68.2%

실험 절차

Method DD was followed (in a round-bottomed flask, reaction time: 20 hours) with N-(4-hydroxynaphthalen-1-yl)acetamide (1.22 g, 6.08 mmol) and 2,6-dichloropyrazine (1.09 g, 7.30 mmol). The DMF was evaporated in vacuo. The resulting crude was dissolved in a mixture (hot) of AcOEt (25 mL) and acetone (175 mL) and filtered. The volume of the filtrate was reduced to 100 mL and this filtrate crystallised upon storage at low temperature to yield the title compound (1.30 g). Yield: 68%. 1H NMR (500 MHz, DMSO-d6) δ 2.21 (s, 3H), 7.42 (d, 1H, J=8.2 Hz), 7.57 (t, 1H, J=7.5 Hz), 7.64 (t, 1H, J=7.6 Hz), 7.72 (d, 1H, J=8.1 Hz), 7.90 (d, 1H, J=8.3 Hz), 8.16 (d, 1H, J=8.5 Hz), 8.52 (s, 1H), 8.72 (s, 1H), 10.02 (s, 1H). 13C NMR (125.8 MHz, DMSO-d6) δ 23.42, 117.59, 121.40, 121.65, 123.42, 126.53, 126.71, 126.85, 128.90, 131.85, 133.59, 137.50, 144.40, 145.04, 158.92, 169.04. m/z 314.0 [(M+H)+ calcd for C16H12ClN3O2 313.1].

후처리

  1. customThe DMF was evaporated in vacuo
  2. dissolutionThe resulting crude was dissolved in a mixture (hot) of AcOEt (25 mL) and acetone (175 mL)
  3. filtrationfiltered
  4. customthis filtrate crystallised upon storage at low temperature

출처 및 근거

ORD 기록
ord-63cbd827c7844c0faa9de21a8c973c2c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737152B2

연결된 노트

불러오는 중…