Sodium Bicarbonate → HCID 178455829、化合物

HRID 44826

反応式

HRID 44826 の反応式
[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.C([O-])(O)=[O:28].[Na+]>C(O)=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]([OH: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

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 58405345(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

生成物 1

HCID 178455829HCID 178455829、化合物収率 80%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 100 mg, 0.28 mmol) was dissolved in 3 mL of HCOOH. This mixture was heated to reflux for 18 h, then aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure and chromatographed on flash silica gel (CH2Cl2:CH3OH=6:1) to give the title compound as a white solid (80 mg, 80% yield). 1H NMR (CD3OD) δ: 8.09 (s, 1H), 8.52 (d, 1H) 7.46 (s, 1H), 7.27 (m, 1H), 4.42-4.38 (m, 2H), 3.41 (s, 3H), 2.0-1.7 (m, 10H) and 0.86 ppm (t, 3H); LCMS: 354.2 m/z (M+H)+; ret. Time: 1.36 min (Analytical Method E).

後処理

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 18 h
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe combined organic phase was dried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on flash silica gel (CH2Cl2:CH3OH=6:1)

出典と根拠

ORDレコード
ord-13ea11e38ec64b1da35e2909c0c974ef
出典データセット
uspto-grants-2013_09
特許番号
US08541418B2

関連ノート

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