Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 1-Cyclopentyl-7-[4-(piperidin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1783512노트

반응식

HRID 1783512 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:14]1([N:19]2[C:24]3=[N:25][C:26](S(C)=O)=[N:27][CH:28]=[C:23]3[CH2:22][NH:21][C:20]2=[O:32])[CH2:18][CH2:17][CH2:16][CH2:15]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.O1CCOCC1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH:14]1([N:19]2[C:24]3=[N:25][C:26]([NH:1][C:2]4[CH:3]=[CH:4][C:5]([N:8]5[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]5)=[CH:6][CH:7]=4)=[N:27][CH:28]=[C:23]3[CH2:22][NH:21][C:20]2=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18]1

참가 물질

7

반응물 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 312751,4-DioxaneHCID 4135014-(Piperidin-1-yl)anilineHCID 688593421-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

생성물 1

HCID 688602801-Cyclopentyl-7-[4-(piperidin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one수율 24%

시약·촉매·용매 2

HCID 6212Chloroform용매4회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 377 mg (2.14 mmol) of 1-(4-aminophenyl)piperidine, 300 mg (1.07 mmol) of 1-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 745 mg (3.21 mmol) of camphorsulfonic acid, and 2 mL of p-dioxane is heated at 130° C. for 1 hour in a sealed tube. The mixture is cooled and diluted with chloroform. The solution is washed twice with saturated aqueous sodium bicarbonate and once each with aqueous sodium chloride then brine. The organic phase is dried over magnesium sulfate and concentrated to leave a dark green residue that is dissolved in chloroform and chromatographed on silica gel eluting with 9:1:0.5 ethyl acetate/ethanol/triethylamine. The product fractions are pooled and concentrated to leave a residue that is dissolved in chloroform. The solution is diluted with ethyl acetate while most of the chloroform is being boiled away. Upon cooling, crystals form and are then collected to leave 101 mg (24%) of the title compound:

후처리

  1. temperatureThe mixture is cooled
  2. washThe solution is washed twice with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto leave a dark green residue that
  6. customchromatographed on silica gel eluting with 9:1:0.5 ethyl acetate/ethanol/triethylamine
  7. concentrationconcentrated
  8. customto leave a residue that
  9. temperatureUpon cooling
  10. customcrystals form and are then collected

출처 및 근거

ORD 기록
ord-509bd9f1df3a469ea279ff706e84076c
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501425B1

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