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

HRID 16314

反応式

HRID 16314 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-72876f7d587a452f848b1116f6fbe5e3
出典データセット
uspto-grants-2010_06
特許番号
US07737152B2

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