Trifluoroacetic acid → HCID 68671843、化合物

HRID 512968ノート

反応式

HRID 512968 の反応式
[NH2:1][C:2]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH3:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=O.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:21][N:18]1[CH2:19][CH2:20][N:15]([C:13]2[CH:12]=[CH:11][C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[C:2]([NH:1][CH:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[CH:14]=2)[CH2:16][CH2:17]1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 13603N-Methyl-2-piperidone2 回HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2 回HCID 667359202-Amino-4-(4-methylpiperazin-1-yl) benzoic acid tertbutyl ester

生成物 1

HCID 68671843HCID 68671843、化合物収率 51%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

tert-Butyl 2-amino-4-(4-methylpiperazin-1-yl)benzoate (1.5 g, 5.15 mmol) was dissolved in dry dioxane (25 mL) under a nitrogen atmosphere. N-methylpiperidone (0.72 g, 6.18 mmol, 1.2 eq) was added, followed by trifluoroacetic acid (1.03 mL, 13.39 mmol, 2.6 eq) and sodium triacetoxyborohydride (1.72 g, 7.73 mmol, 1.5 eq). The mixture was stirred at room temperature for 26 hours. During this time extra portions of N-methylpiperidone (0.5 mL, 0.75 eq) and sodium triacetoxyborohydride (1.72 g, 7.73 mmol, 1.5 eq) were added. A saturated aqueous solution of NaHCO3 was then added and the reaction mixture was concentrated under reduced pressure. 10% ammonium hydroxide was added until pH 10 and the aqueous phase was extracted with dichloromethane. The organic phase was washed with brine, dried over Na2SO4 and evaporated under reduced pressure. After purification by chromatography over silica gel (DCM/MeOH/NH3 7% in MeOH 90:8:2) 1.025 g of title compound were obtained as off-white solid (51% yield).

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. addition10% ammonium hydroxide was added until pH 10
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customAfter purification by chromatography over silica gel (DCM/MeOH/NH3 7% in MeOH 90:8:2) 1.025 g of title compound

出典と根拠

ORDレコード
ord-98828f0716b64c91bd0b5bd7342c4ac4
出典データセット
uspto-grants-2015_08
特許番号
US09102662B2

反応ノート

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