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

HRID 16278

反応式

HRID 16278 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.[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-63cbd827c7844c0faa9de21a8c973c2c
出典データセット
uspto-grants-2010_06
特許番号
US07737152B2

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