Sodium cyanoborohydride → 7-chloro-3-(3,5-dimethylphenyl)-4-{1-[4-(4-methoxyphenyl)-butyl]-piperidin-2-yl-methoxy}-1H-quinolin-2-one

HRID 1857605

반응식

HRID 1857605 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][CH:40]=O)=[CH:33][CH:32]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][N:24]3[CH2:40][CH2:39][CH2:38][CH2:37][C:34]3[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:36][CH:35]=3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 104875554-(4-Methoxyphenyl)butanalHCID 221300057-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one

생성물 1

HCID 540325717-chloro-3-(3,5-dimethylphenyl)-4-{1-[4-(4-methoxyphenyl)-butyl]-piperidin-2-yl-methoxy}-1H-quinolin-2-one

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one (prepared essentially as described in Example 10, 34 mg in 3.0 mL dry methanol) was added 18 mg of 4-(4-methoxyphenyl)-butyraldehyde, 150 mg powdered 4 Å molecular sieves and one drop of acetic acid. After 30 minutes, 0.13 mL of a 1M solution of sodium cyanoborohydride in tetrahydrofuran was added and the mixture stirred at room temperature for 18 hours. At this time the reaction mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. Purification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3) gave the title compound, 39 mg.

후처리

  1. filtrationAt this time the reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3)

출처 및 근거

ORD 기록
ord-4b565d37fcf64e1fbf76b1d070a774de
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147088

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