Acetic Acid → 6-Chloro-8-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline

HRID 2241980노트

반응식

HRID 2241980 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N:19]1([C:25]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:26]=2[CH:27]=[CH:28][NH:29]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>C(Cl)Cl.ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([N:22]4[CH2:23][CH2:24][N:19]([C:25]5[CH:33]=[CH:32][CH:31]=[C:30]6[C:26]=5[CH:27]=[CH:28][NH:29]6)[CH2:20][CH2:21]4)[CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 592048441-(6-Chloro-8-quinolinyl)-4-piperidinone

생성물 1

HCID 120042826-Chloro-8-{4-[4-(1H-indole-4-yl)-1-piperazinyl]-1-piperidinyl}quinoline

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 1-(6-chloro-quinolin-8-yl)-piperidin-4-one (Step 1, 0.13 g) and of 4-piperazino-indole (commercially available, 0.100 g) in 15 mL CH2Cl2 in 10 mL of dichloroethane, was added 0.137 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 was filtered through 100 ml of silica gel using 100% Ethyl acetate, to give 0.070 g of the desired product. Mp: 224° C.; MS (ES) m/z (relative intensity): 447 (M++−H, 100).

후처리

  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 100 ml of silica gel using 100% Ethyl acetate

출처 및 근거

ORD 기록
ord-e1cc4a6096f6499fb475cf1fcbfc5965
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671056B2

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