Sodium Carbonate → HCID 58405527, 화합물

HRID 44830노트

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HRID 44830 반응식
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:27]([CH3:29])[CH3:28].Cl.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([N:27]([CH3:29])[CH3:28])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 10473Dimethylamine, hydrochlorideHCID 58405345(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

생성물 1

HCID 58405527HCID 58405527, 화합물수율 61%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
140 °C

실험 절차

To the solution of (R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 200 mg, 0.56 mmol) in 5 mL of DMSO, (CH3)2NH HCl (200 mg 5.6 mmol) and Na2CO3 (130 mg, 1.2 mmol) were added. The mixture was heated to 140° C. for 18 hr in a sealed tube, quenched with water and extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure, and chromatographed (CH2Cl2:CH3OH=15:1) to give the title compound as a white solid (130 mg, 60% yield). 1H NMR (CDCl3) δ: 8.27 (d, 1H), 7.97 (s, 1H) 7.49 (s, 1H), 7.43 (d, 1H), 4.35-4.29 (m, 2H), 3.39 (s, 3H), 3.18 (s, 6H), 2.1-1.7 (m, 10H) and 0.87 ppm (t, 3H); LCMS: 381.3 m/z (M+H)+; ret. Time: 1.44 min (Analytical Method E).

후처리

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phase was dried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed (CH2Cl2:CH3OH=15:1)

출처 및 근거

ORD 기록
ord-80449104f2044a92a302f24543357069
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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