Methylamine → HCID 58405769, 화합물

HRID 44829노트

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HRID 44829 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.[CH3:27][NH2:28]>CCN(CC)CC>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:28][CH3:27])[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

4

반응물 2

HCID 6329MethylamineHCID 58405345(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

생성물 1

HCID 58405769HCID 58405769, 화합물수율 70%

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
110 °C

실험 절차

To a 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 methylamine (5 mL of 2M in CH3OH), 1 mL of Et3N was added. The mixture was stirred at 110° C. in a sealed tube for 18 h, and then concentrated under reduced pressure, quenched with water and extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure, and chromatographed (CH2Cl2:CH3OH=10:1) to give the title compound as a white solid (150 mg, 70% yield). 1H NMR (CDCl3) δ: 9.76 (broad, 1H), 8.08 (s, 1H) 7.85 (d, 1H), 7.74 (s, 1H), 7.58 (d, 1H), 4.40 (m, 2H), 3.43 (s, 3H), 3.1 (s, 3H), 2.2-1.7 (m, 10H) and 0.89 ppm (t, 3H); LCMS: 367.2 m/z (M+H)+; ret. Time: 1.44 min (Analytical Method E).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phase was dried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed (CH2Cl2:CH3OH=10:1)

출처 및 근거

ORD 기록
ord-f2c472cc80c14b8fa1ff403c98af04ae
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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