Trifluoroacetic acid → HCID 68671843, 화합물

HRID 1773402노트

반응식

HRID 1773402 반응식
[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

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 13603N-Methyl-2-piperidone2회HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2회HCID 667359202-Amino-4-(4-methylpiperazin-1-yl) benzoic acid tertbutyl ester

생성물 1

HCID 68671843HCID 68671843, 화합물수율 51%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fad91913269c445eab57965ebd9e5dde
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255087B2

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