Triethylamine → (R)-1-{4-[4-(3-Chloro-benzylidene)-piperidin-1-yl]-pyrimidin-2-yl}-ethyl butyrate

HRID 431666ノート

反応式

HRID 431666 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH:6]=[C:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH2:16](N(CC)CC)[CH3:17].[C:23]([O:26][C@@H:27]([C:29]1[N:34]=[C:33](Cl)[CH:32]=[CH:31][N:30]=1)[CH3:28])(=[O:25])[CH3:24]>ClCCl>[C:23]([O:26][C@@H:27]([C:29]1[N:34]=[C:33]([N:10]2[CH2:11][CH2:12][C:7](=[CH:6][C:5]3[CH:13]=[CH:14][CH:15]=[C:3]([Cl:2])[CH:4]=3)[CH2:8][CH2:9]2)[CH:32]=[CH:31][N:30]=1)[CH3:28])(=[O:25])[CH2:24][CH2:16][CH3:17]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 223286604-(3-Chlorobenzylidene)-piperidine hydrochlorideHCID 54154993(R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate

生成物 1

HCID 53807001(R)-1-{4-[4-(3-Chloro-benzylidene)-piperidin-1-yl]-pyrimidin-2-yl}-ethyl butyrate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-(3-chlorobenzylidene)-piperidine hydrochloride (prepared according to the method of Example 176, Step: B, 0.46 g, 2.0 mmol) and triethylamine (0.61 g, 6.0 mmol) in dichloromethane (10 mL) was added (R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate (prepared according to the method of Preparation Five, 0.54 g, 2.2 mmol) and stirred at ambient temperature for 12 h. The mixture was washed successively with saturated aqueous sodium bicarbonate and water, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated to obtain a crude product which was purified by flash chromatography (95:5 dichloromethane:methanol) to give the title compound of Example 176, Step C as a viscous oil, 0.64 g (80%). 1H NMR (CDCl3, 300 MHz) δ 0.95 (d, 6H), 1.51 (d, 3H), 1.68 (m, 2H) 2.35 (m, 2H), 2.47-2.64 (m, 4H), 3.67-3.75 (m, 4H), 5.68 (q, 1H), 6.36 (s, 1H), 6.40 (d, 1H), 6.98 (m, 1H), 7.12-7.28 (m, 3H), 8.18 (m, 1H); MS (Cl) 400 (MH+).

後処理

  1. customprepared
  2. customaccording to the method of Preparation Five, 0.54 g, 2.2 mmol) and
  3. washThe mixture was washed successively with saturated aqueous sodium bicarbonate and water
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto obtain a crude product which
  8. customwas purified by flash chromatography (95:5 dichloromethane:methanol)

出典と根拠

ORDレコード
ord-3a6d011a01b24b7982ed5435b25fe354
出典データセット
uspto-grants-2003_12
特許番号
US06660740B1

反応ノート

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