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

HRID 1532323노트

반응식

HRID 1532323 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-774078c4f18340bd98aa1dd786bbece3
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06201024B1

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