Sodium triacetoxyborohydride → 5-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinoline

HRID 2241970ノート

反応式

HRID 2241970 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N:19]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]=[CH:30]3)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([N:22]3[CH2:23][CH2:24][N:19]([C:25]4[CH:26]=[CH:27][CH:28]=[C:29]5[C:34]=4[N:33]=[CH:32][CH:31]=[CH:30]5)[CH2:20][CH2:21]3)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 118307868-(1-piperazinyl)QuinolineHCID 592048481-(5-Fluoroquinolin-8-yl)piperidin-4-one

生成物 1

HCID 120041965-Fluoro-8-{4-[4-(8-quinolinyl)-1-piperazinyl]-1-piperidinyl]quinoline収率 138.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 0.120 g of 1-(5-fluoro-quinolin-8-yl)-piperidin-4-one (Step 3, 0.22 g) and 8-piperazin-1-ylquinoline (Oruz, et al., J. Med. Chem. 45:4128 (2002), 0.19 g) was added of 0.19 g sodium triacetoxyborohydride and 0.1 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water and dried over magnesium sulfate. The product was filtered through 75 ml of silica gel using 100% Ethyl acetate, to give 0.30 g of the desired product. Mp: 224° C.; MS (ES) m/z (relative intensity): 442 (M++−H, 100).

後処理

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered through 75 ml of silica gel using 100% Ethyl acetate

出典と根拠

ORDレコード
ord-4ef313efd6094420b4278fbfa58941dc
出典データセット
uspto-grants-2010_03
特許番号
US07671056B2

反応ノート

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