Acetic Acid → 6-Fluoro-8-{4-[1-(8-quinolinyl)-4-piperidinyl]-1-piperazinyl}quinoline

HRID 2241968

反応式

HRID 2241968 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[N:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)[CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH:31]4[CH2:30][CH2:29][N:28]([C:26]5[CH:25]=[CH:24][CH:23]=[C:22]6[C:27]=5[N:18]=[CH:19][CH:20]=[CH:21]6)[CH2:33][CH2:32]4)[CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 589754886-Fluoro-8-(piperazin-1-yl)quinolineHCID 592048421-Quinolin-8-yl-piperidin-4-one

生成物 1

HCID 120041126-Fluoro-8-{4-[1-(8-quinolinyl)-4-piperidinyl]-1-piperazinyl}quinoline収率 45.4%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

To a solution of 0.247 g of 6-fluoro-8-piperazino-quinoline (Step 3) in 10 mL of dichloroethane, was added 0.226 g of 1-quinolin-8-yl-piperidin-4-one (Example A, Step 6, above) followed by 0.274 g of 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 crystallized and filtered to give 0.200 g of the desired product. Mp: 211° 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. customThe product crystallized
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-15e277b2b500461b9ea0927b56b83a7f
出典データセット
uspto-grants-2010_03
特許番号
US07671056B2

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