Benzylethanolamine → 2-[Benzyl({5-[benzyl(1-methylethyl)amino]-3-chloropyrazin-2-yl}methyl)amino]ethanol

HRID 1879728노트

반응식

HRID 1879728 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([N:22]([CH:32]([CH3:34])[CH3:33])[C:23]1[N:24]=[C:25]([Cl:31])[C:26]([CH:29]=O)=[N:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:35]([NH:42][CH2:43][CH2:44][OH:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:35]([N:42]([CH2:29][C:26]1[C:25]([Cl:31])=[N:24][C:23]([N:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:32]([CH3:34])[CH3:33])=[CH:28][N:27]=1)[CH2:43][CH2:44][OH:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

7

반응물 4

HCID 4348BenzylethanolamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866489995-[Benzyl(1-methylethyl)amino]-3-chloropyrazine-2-carbaldehyde

생성물 1

HCID 866490002-[Benzyl({5-[benzyl(1-methylethyl)amino]-3-chloropyrazin-2-yl}methyl)amino]ethanol수율 94%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

Sodium triacetoxyborohydride (2.65 g) was added to a solution of 5-[benzyl(1-methylethyl)amino]-3-chloropyrazine-2-carbaldehyde (2.42 g), N-benzylethanolamine (1.42 g) and acetic acid (1.43 mL) in acetonitrile (14 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was basified with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 20→50% ethyl acetate/hexane) to give the title compound (3.32 g, 94%) as a pale-yellow oil.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe aqueous layer was extracted again with ethyl acetate
  3. washThe combined organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (solvent gradient: 20→50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-acdb84b15fb84bac880363c123e277f9
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318722B2

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