Chloroacetaldehyde → 2-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 1532323ノート

反応式

HRID 1532323 の反応式
[Cl:1][CH2:2][CH:3]=O.[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:26])=[C:10]([CH:25]=1)[C:11]([NH:13][CH2:14][C:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2)=[O:12].Cl.C([BH3-])#N.[Na+]>CO>[Cl:26][C:9]1[CH:8]=[CH:7][C:6]([NH:5][CH2:3][CH2:2][Cl:1])=[CH:25][C:10]=1[C:11]([NH:13][CH2:14][C:15]12[CH2:16][CH:17]3[CH2:23][CH:21]([CH2:20][CH:19]([CH2:18]3)[CH2:24]1)[CH2:22]2)=[O:12]

参加物

6

反応物 4

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 227314875-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

生成物 1

HCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Chloroacetaldehyde (50% solution in water) (0.705 ml) was added to a solution of amino amide from Example 55 (1.5 g) in methanol (15 ml). After 10 minutes hydrochloric acid (0.77 ml of a 50% solution in methanol) was added. Solid sodiumcyanoborohydride (0.317 g) was added and the mixture stirred at ambient temperature for two days. The solvent was removed under reduced pressure, the residue was dissolved in dichloromethane (50 ml) and washed with aqueous sodium hydrogen carbonate (3×50 ml). The organic extracts were dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with hexane:diethylether (1:1) to give the title compound as a yellow solid (1.13 g).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (50 ml)
  3. washwashed with aqueous sodium hydrogen carbonate (3×50 ml)
  4. dry with materialThe organic extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with hexane:diethylether (1:1)

出典と根拠

ORDレコード
ord-774078c4f18340bd98aa1dd786bbece3
出典データセット
uspto-grants-2001_03
特許番号
US06201024B1

反応ノート

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