Dihydro-3(2H)-thiophenone → 5-Chloro-N-(5-methylpyridin-2-yl)-2-{[1-(tetrahydrothiophen-3-yl)piperidin-4-yl]methylamino}benzamide

HRID 1883017

반응식

HRID 1883017 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1)=[O:8].[S:26]1[CH2:30][CH2:29][C:28](=O)[CH2:27]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:28]3[CH2:29][CH2:30][S:26][CH2:27]3)[CH2:22][CH2:21]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1)=[O:8]

참가 물질

6

반응물 3

HCID 61252Dihydro-3(2H)-thiophenoneHCID 5003444Sodium cyanoborohydrideHCID 219063095-Chloro-N-(5-methylpyridin-2-yl)-2-[(4-piperidinylmethyl)amino]benzamide

생성물 1

HCID 219063215-Chloro-N-(5-methylpyridin-2-yl)-2-{[1-(tetrahydrothiophen-3-yl)piperidin-4-yl]methylamino}benzamide수율 77.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 10129899Acetic acid methanol용매

반응 조건

온도
50 °C

실험 절차

A solution of 5-chloro-N-(5-methylpyridin-2-yl)-2-[(4-piperidinylmethyl)amino]benzamide from Example 99-A (0.45 g, 1.25 mmol) in 10 mL of 95:5 methanol-acetic acid was treated with excess tetrahydrothiophen-3-one (1.07 mL, 12.5 mmol), followed by sodium cyanoborohydride (5.0 ml of a 1 M solution in tetrahydrofuran, 6.0 mmol). After stirring at 50° C. for 96 h, the mixture was concentrated in vacuo; and the residue was subjected to silica gel chromatography. Elution with 9:1 dichloromethane-2 M ammonia in methanol afforded 0.43 g (77%) of the title compound as a yellow solid.

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. washElution with 9:1 dichloromethane-2 M ammonia in methanol

출처 및 근거

ORD 기록
ord-b4b22624256047f284aa275ed0a8c527
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759414B2

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