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p-Toluenesulfonic acid → methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate

HRID 2364682
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HRID 2364682 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([O:15][CH3:16])=[O:14])=[C:6]2[C:10]=1[O:9][C:8]([CH3:12])([CH3:11])[CH2:7]2.Cl[C:18]1[N:27]=[CH:26][C:25]2[N:24]([CH3:28])[C:23](=[O:29])[C@@H:22]([CH2:30][CH3:31])[N:21]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:20]=2[N:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(O)CC(C)C>[CH:32]1([N:21]2[C:20]3[N:19]=[C:18]([NH:1][C:2]4[CH:3]=[CH:4][C:5]([C:13]([O:15][CH3:16])=[O:14])=[C:6]5[C:10]=4[O:9][C:8]([CH3:12])([CH3:11])[CH2:7]5)[N:27]=[CH:26][C:25]=3[N:24]([CH3:28])[C:23](=[O:29])[C@H:22]2[CH2:30][CH3:31])[CH2:33][CH2:34][CH2:35][CH2:36]1
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참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneHCID 68107595Methyl 7-amino-2,2-dimethyl-2,3-dihydrobenzofuran-4-carboxylate

생성물 1

HCID 68107267methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate
수율 106.7%

시약·촉매·용매 1

HCID 79104-Methyl-2-Pentanol용매

실험 절차

Methyl 7-amino-2,2-dimethyl-3H-benzofuran-4-carboxylate 4d (770 mg, 3.48 mmol) was dissolved in 20 mL of 1,3-dimethyl-butanol followed by the addition of (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (1.23 g, 4.18 mmol) and p-toluenesulfonic acid (1.06 g, 5.57 mmol) successively. The reaction solution was heated to reflux for 2 hours with stirring. The resulting solution was added with 50 mL of saturated sodium bicarbonate solution, extracted with ethyl acetate (50 mL×3). The combined organic phase was washed with water (30 mL), saturated sodium chloride solution (20 mL) successively and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate 4e (1.78 g, yield: 100%) as a light yellow solid.

후처리

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. washThe combined organic phase was washed with water (30 mL), saturated sodium chloride solution (20 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-01152de87ca1492d95c25142be2a67b7
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691822B2

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