Benzaldehyde → N-{(1S)-1-[3-(benzylamino)phenyl]ethyl}-6-chloropyrazin-2-amine

HRID 572204

반응식

HRID 572204 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([C@@H:16]([NH:18][C:19]2[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=2)[CH3:17])[CH:13]=[CH:14][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH2:1]([NH:9][C:10]1[CH:11]=[C:12]([C@@H:16]([NH:18][C:19]2[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=2)[CH3:17])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 25218447(S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine

생성물 1

HCID 59331714N-{(1S)-1-[3-(benzylamino)phenyl]ethyl}-6-chloropyrazin-2-amine수율 97.4%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of benzaldehyde (0.1 mL, 1 mmol) and N-[(1S)-1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (248 mg, 1 mmol) in dichloroethane (5 mL) was added sodium triacetoxyborohydride (300 mg, 1.4 mmol) in one portion and the mixture was stirred at room temperature for 16 hours. After this time a solution of saturated aqueous sodium hydrogen carbonate (20 mL) was added and the mixture was stirred for 10 minutes. The mixture was extracted with ethyl acetate (2×20 mL) and the extracts washed with brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give N-{(1S)-1-[3-(benzylamino)phenyl]ethyl}-6-chloropyrazin-2-amine (330 mg, 97%) as an off white solid of reasonable purity.

후처리

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  3. washthe extracts washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dfdcbc5ab07946f69142616c23de0336
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029386B2

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