Sodium Bicarbonate → 3-amino-4-({3-[benzyl(methyl)amino]propyl}amino)-N,N-diisobutylbenzamide

HRID 883683

반응식

HRID 883683 반응식
O.O.[Sn](Cl)(Cl)(Cl)Cl.[CH2:8]([N:15]([CH3:40])[CH2:16][CH2:17][CH2:18][NH:19][C:20]1[CH:36]=[CH:35][C:23]([C:24]([N:26]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])=[CH:22][C:21]=1[N+:37]([O-])=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[NH2:37][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][C:20]=1[NH:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:40])[C:24]([N:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:25]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 690273444-({3-[benzyl(methyl)amino]propyl}amino)-N,N-diisobutyl-3-nitrobenzamideHCID 85782573Tin tetrachloride dihydrate

생성물 1

HCID 690287923-amino-4-({3-[benzyl(methyl)amino]propyl}amino)-N,N-diisobutylbenzamide수율 78%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

Tin chloride dihydrate (3.58 g, 5 eq) is added to a solution of 4-({3-[benzyl(methyl)amino]propyl}amino)-N,N-diisobutyl-3-nitrobenzamide (1.44 g, prepared according to the procedure described for Example A1), in ethyl acetate (40 ml). The mixture is heated under reflux for 7 hours then cooled down to a temperature of approximately 20° C. and poured into a saturated solution of NaHCO3. After decanting and extracting with ethyl acetate, the organic phases are combined, washed with salt water, dried over sodium sulphate and concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent dichloromethane/methanol 95:5) produces the compound in the form of a foam (1.06 g, 78% yield).

후처리

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 7 hours
  4. customAfter decanting
  5. extractionextracting with ethyl acetate
  6. washwashed with salt water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure at 40° C
  9. customPurification by flash chromatography on silica gel (eluent dichloromethane/methanol 95:5)

출처 및 근거

ORD 기록
ord-61d7f3c3efaf4428b177ff41f580fd60
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236965B2

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