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Pyridine → 8-(2,6-Difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-[2-(5-oxo-4,5-dihydro-[1,2,4]-oxadiazol-3-yl)-ethylamino)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2252910
ノート
印刷プレビュー

反応式

HRID 2252910 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][CH2:29][C:30]([NH:32][OH:33])=[NH:31])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:34].N1C=CC=CC=1.Cl[C:42](OCC(CC)CCCC)=[O:43]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][CH2:29][C:30]3[NH:31][C:42](=[O:43])[O:33][N:32]=3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 178427842HCID 178427842、化合物

生成物 1

HCID 1360762378-(2,6-Difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-[2-(5-oxo-4,5-dihydro-[1,2,4]-oxadiazol-3-yl)-ethylamino)-8H-pyrido[2,3-d]pyrimidin-7-one収率 28.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Under Ar, to a soln of the product of Example 242, 3-[8-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-N-hydroxy-propionamidine (100 mg, 0.20 mmol), and pyridine (0.048 mL, 0.6 mmol), was added 2-ethylhexyl chloroformate (0.039 mL, 0.2 mmol). The mixture was stirred at room temperature for 2 h, then diluted with H2O and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated. The resulting residue was diluted with xylene (10 mL) and heated to reflux for 18 h to give the crude material, which was purified by preparative hplc to give the desired product 28 mg (28%). LC-MS: 495.0 (MH+, m/z), 1.96 (Rt, min).

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe resulting residue was diluted with xylene (10 mL)
  6. temperatureheated
  7. temperatureto reflux for 18 h
  8. customto give the crude material, which
  9. customwas purified by preparative hplc

出典と根拠

ORDレコード
ord-1064c28636f041c0a8af70e173b6bcb7
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07323472B2

反応ノート

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