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

HRID 2364666노트

반응식

HRID 2364666 반응식
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:31]([O:33][CH3:34])=[O:32])=[C:26]2[C:30]=1[O:29][CH2:28][CH2:27]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(C)CC(O)C>[CH:16]1([N:5]2[C:4]3[N:3]=[C:2]([NH:21][C:22]4[CH:23]=[CH:24][C:25]([C:31]([O:33][CH3:34])=[O:32])=[C:26]5[C:30]=4[O:29][CH2:28][CH2:27]5)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]2[CH2:14][CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

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 68107686Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate

생성물 1

HCID 68107956methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylate수율 74.1%

시약·촉매·용매 1

HCID 79104-Methyl-2-Pentanol용매

실험 절차

(7R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (670 mg, 2.30 mmol), methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate 1g (440 mg, 2.30 mmol) and p-toluenesulfonic acid (700 mg, 3.68 mmol) were dissolved in 25 mL 4-methyl-2-pentanol. The resulting solution was heated to reflux for 6 hours with stirring. The reaction solution was added with 25 mL of saturated sodium bicarbonate solution, extracted with ethyl acetate (50 mL×3). The combined organic phase was washed with water (50 mL×3) and saturated sodium chloride solution (50 mL×3) successively, then dried over anhydrous sodium sulfate, filtered and 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]-2,3-dihydrobenzofuran-4-carboxylate 1p (0.77 g, yield: 74.0%) as a light yellow solid.

후처리

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

출처 및 근거

ORD 기록
ord-7de742ec94ae46649af527cdc74b64ab
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691822B2

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