Triethylamine → (R)-1-[4-(4-Oxazolo[5,4-c]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethyl butyrate

HRID 431643ノート

反応式

HRID 431643 の反応式
[N:1]1([C:7]2[O:8][C:9]3[CH:10]=[N:11][CH:12]=[CH:13][C:14]=3[N:15]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:16]([O:21][C@@H:22]([C:24]1[N:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1)[CH3:23])(=[O:20])[CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>C(O)(C)C>[C:16]([O:21][C@@H:22]([C:24]1[N:25]=[C:26]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[O:8][C:9]4[CH:10]=[N:11][CH:12]=[CH:13][C:14]=4[N:15]=3)[CH2:2][CH2:3]2)[CH:27]=[CH:28][N:29]=1)[CH3:23])(=[O:20])[CH2:17][CH2:18][CH3:19]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 100587322-(1-Piperazinyl)oxazolo[5,4-c]pyridineHCID 10944226(R)-1-(4-chloro-pyrimidin-2-yl)ethyl butyrate

生成物 1

HCID 11133045(R)-1-[4-(4-Oxazolo[5,4-c]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethyl butyrate収率 79%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a solution of 2-(1-piperazinyl)oxazolo[5,4-c]pyridine (775 mg, 3.8 mmol; J. Org. Chem. 1995, 60, 5721) in isopropanol (38 mL) was added (R)-1-(4-chloro-pyrimidin-2-yl)-ethyl butyrate (prepared according to the method of Preparation Seven, 868 mg, 3.8 mmol) followed by triethylamine (1.6 mL, 11.4 mmol). This mixture was stirred at reflux overnight, cooled to room temperature, and evaporated. The residue was diluted with saturated aqueous sodium bicarbonate and extracted with chloroform (3×). The combined organic extracts were dried over sodium sulfate, filtered, evaporated, and purified by flash column chromatography (2×; 3% methanol/chloroform then 6→8% methanol/ethyl acetate, where used herein, the arrow symbol, →, indicates a gradient) to give 1.2 g (79%) of the title compound of Example 2, Step A as a pale yellow oil which solidified upon standing. 1H NMR (CDCl3, 250 MHz) δ 8.57 (s, 1H), 8.39 (d, 1H), 8.28 (d, 1H), 7.30 (d, 1H), 6.44 (d, 1H), 5.70 (q, 1H), 3.85 (s, 8H), 2.42 (t, 2H), 1.78-1.61 (c, 2H), 1.60 (d, 3H), 0.98 (t, 3H); MS (APCI) 397 (MH+).

後処理

  1. customprepared
  2. customaccording to the method of Preparation Seven, 868 mg, 3.8 mmol)
  3. temperatureat reflux overnight
  4. customevaporated
  5. additionThe residue was diluted with saturated aqueous sodium bicarbonate
  6. extractionextracted with chloroform (3×)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by flash column chromatography (2×

出典と根拠

ORDレコード
ord-00296a93df4b4931a397c2d1a2609488
出典データセット
uspto-grants-2003_12
特許番号
US06660740B1

反応ノート

読み込み中…