Acetic Acid → N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

HRID 1247607ノート

反応式

HRID 1247607 の反応式
[C:1]12([CH2:11][NH:12][C:13](=[O:23])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:21]=C)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(O)(=[O:26])C>ClCCl>[C:1]12([CH2:11][NH:12][C:13](=[O:23])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:21]=[O:26])[CH:15]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

参加物

4

反応物 2

HCID 176Acetic AcidHCID 21906707N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide

生成物 1

HCID 21906741N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide (Example 29(i)) (1.70 g) was dissolved in dichloromethane (50 mL), treated with acetic acid (1 mL) and cooled to −78° C. under nitrogen. Ozone was bubbled through the resulting solution for 2 hours while maintaining the temperature. Nitrogen was subsequently bubbled through the solution for 10 minutes and dimethylsulfide (2 mL) was added. The solution was warmed to room temperature washed with sodium bicarbonate (2×10 mL) and brine (30 mL); the organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20) to afford the sub-titled compound (1.13 g).

後処理

  1. customOzone was bubbled through the resulting solution for 2 hours
  2. temperaturewhile maintaining the temperature
  3. customNitrogen was subsequently bubbled through the solution for 10 minutes
  4. additiondimethylsulfide (2 mL) was added
  5. temperatureThe solution was warmed to room temperature
  6. washwashed with sodium bicarbonate (2×10 mL) and brine (30 mL)
  7. dry with materialthe organics were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20)

出典と根拠

ORDレコード
ord-01fbfe563b2c4ee481ced2672ef9c963
出典データセット
uspto-grants-2006_10
特許番号
US07129246B2

反応ノート

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