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

HRID 16314

반응식

HRID 16314 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.CC(C)([O-])C.[K+].[Cl:22][C:23]1[CH:28]=[N:27][CH:26]=[C:25](Cl)[N:24]=1>CN(C=O)C>[Cl:22][C:23]1[N:24]=[C:25]([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:26]=[N:27][CH:28]=1

참가 물질

5

반응물 3

HCID 785042,6-DichloropyrazineHCID 235848N-(4-hydroxynaphthalen-1-yl)acetamideHCID 23665647Potassium tert-butoxide

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

Method KK. A mixture of N-(4-hydroxynaphthalen-1-yl)acetamide (1.22 g, 6.08 mmol) and potassium tert-butoxide (0.68 g, 6.08 mmol) in dry DMF (19 mL) was stirred for 1 hour under argon. To this mixture, 2,6-dichloropyrazine (1.09 g, 7.30 mmol) was added and the temperature was raised to 90° C. and maintained for 20 hours. The DMF was evaporated in vacuo. The resulting crude was dissolved in a (hot) mixture 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. temperaturemaintained for 20 hours
  2. customThe DMF was evaporated in vacuo
  3. dissolutionThe resulting crude was dissolved in a (hot) mixture of AcOEt (25 mL) and acetone (175 mL)
  4. filtrationfiltered
  5. customthis filtrate crystallised upon storage at low temperature

출처 및 근거

ORD 기록
ord-72876f7d587a452f848b1116f6fbe5e3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737152B2

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