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

HRID 883683ノート

反応式

HRID 883683 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-61d7f3c3efaf4428b177ff41f580fd60
出典データセット
uspto-grants-2012_08
特許番号
US08236965B2

反応ノート

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