Acetic Anhydride → HCID 57585054、化合物

HRID 2077621ノート

反応式

HRID 2077621 の反応式
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3[CH:11]=[C:12]([OH:17])[C:13]([Cl:16])=[N:14][CH:15]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:18]([O:17][C:12]1[C:13]([Cl:16])=[N:14][CH:15]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)[CH:11]=1)(=[O:20])[CH3:19]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 57585037HCID 57585037、化合物

生成物 1

HCID 57585054HCID 57585054、化合物収率 37.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

A dry 5 mL, one neck round bottom flask was charged with 5-(benzo[d]thiazol-6-yl)-2-chloropyridin-3-ol (0.0120 g, 0.046 mmol), a stirbar, 0.5 mg DMAP and 1 mL anhydrous pyridine. The flask was fitted with an inert atmosphere inlet. The solution was treated with acetic anhydride (0.017 ml, 0.18 mmol), and the inert atmosphere needle was removed. The closed system was heated in a 60° C. oil bath for 60 minutes, and cooled. The solution was concentrated in vacuo, and purified using a 19×150 mm Waters Xterra Prep C18 OBD column (100 Å pore diameter, 5 μm particle size, spherical shape, PN 186002381; Gradient: 0→5 min@20 mL/min, 25% B; 5.0→35 min@20 mL/min, linear gradient to 55% B; 35→45@20 mL/min, isocratic at 55% B, 45→55 min@20 mL/min, step to 100% B; 55→60 min@20 mL/min, step to 25% B; 60 min end; A=water; B=2% TFE in ACN). A band that eluted from 21.3 to 23.3 minutes was isolated. The solvent was removed in vacuo to afford 5-(benzo[d]thiazol-6-yl)-2-chloropyridin-3-yl acetate (0.0052 g, 37% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 2.43 (s) 7.71 (dd) 7.78 (d) 8.16 (d) 8.24 (d) 8.58 (d) 9.08 (s). 13C NMR (101 MHz, chloroform-d) δ ppm 20.79 (s) 120.61 (s) 124.38 (s) 125.67 (s) 130.70 (s) 133.35 (s) 134.97 (s) 136.67 (s) 143.53 (s) 143.81 (s) 144.86 (s) 153.46 (s) 155.23 (s) 168.08 (s). HPLC-MS: 2.09 min (92.8%@215 nm; 95.0% @254 nm; m/z=305.0, calculated for C14H9ClNO2S+H+=305.0).

後処理

  1. customThe flask was fitted with an inert atmosphere inlet
  2. customthe inert atmosphere needle was removed
  3. temperaturecooled
  4. concentrationThe solution was concentrated in vacuo
  5. custompurified
  6. custom0→5 min@20 mL/min, 25% B
  7. custom5.0→35 min@20 mL/min, linear gradient
  8. customisocratic at 55% B, 45→55 min@20 mL/min, step
  9. custom55→60 min@20 mL/min, step
  10. custom60 min end
  11. washA band that eluted from 21.3 to 23.3 minutes
  12. customwas isolated
  13. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-c6f73e9bf315441b9391b6bab036de33
出典データセット
uspto-grants-2011_04
特許番号
US07928140B2

反応ノート

読み込み中…