Acetic Acid → 1-methyl-3-({[2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethyl]amino}methyl)quinolin-2(1H)-one

HRID 1943020

반응식

HRID 1943020 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH:12]=O)[C:3]1=[O:14].C([O-])(=O)C.[Na+].[Cl-].[C:21]1([CH:27]([CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH2:28][NH3+:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][NH:29][CH2:28][CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[C:3]1=[O:14]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 673936932-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethanaminium chloride

생성물 1

HCID 584159371-methyl-3-({[2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethyl]amino}methyl)quinolin-2(1H)-one

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (35 mg, 0.187 mmol), sodium acetate (19.94 mg, 0.243 mmol), and 2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethanaminium chloride (45.2 mg, 0.187 mmol) were combined in 1,2 dichloroethane (2 ml). Acetic acid (0.021 ml, 0.374 mmol) and sodium triacetoxyborohydride (119 mg, 0.561 mmol) were added and the reaction stirred for 20 hours. The mixture was partitioned between CH2Cl2 and satd. bicarb and the aqueous portion was extracted 3×CH2Cl2. The organic portion was dried (Na2SO4) and concentrated in vacuo. The resulting material was purified by reversed-phase chromatography (10-60% ACN in water (with 2 ml/l NH4OH) over 20 min at 20 ml/min, 20×100 mm Phenomenex Gemini C18 column). Desired fractions were concentrated in vacuo. 50.5 mg, 73%.

후처리

  1. customThe mixture was partitioned between CH2Cl2 and satd
  2. extractionbicarb and the aqueous portion was extracted 3×CH2Cl2
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting material was purified by reversed-phase chromatography (10-60% ACN in water (with 2 ml/l NH4OH) over 20 min at 20 ml/min, 20×100 mm Phenomenex Gemini C18 column)
  6. concentrationDesired fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-50dcf7ee4d7f482ebf7fc6e8c48bf8e5
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389720B2

연결된 노트

불러오는 중…