Pyridine → N,N'-Di-tert-butoxycarbonyl-7-(1-benzylsulfonylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine

HRID 412567노트

반응식

HRID 412567 반응식
[C:1]([O:5][C:6]([NH:8][C:9]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:23][CH:24]=2)[CH2:19]1)=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:42]1([CH2:48][S:49](Cl)(=[O:51])=[O:50])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1.CN(C)C1C=CN=CC=1>[C:14]([O:13][C:11]([NH:10][C:9]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]3[CH2:35][CH2:34][N:33]([S:49]([CH2:48][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)(=[O:51])=[O:50])[CH2:32][CH2:31]3)=[CH:23][CH:24]=2)[CH2:19]1)=[N:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:12])([CH3:17])([CH3:16])[CH3:15]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 60064218N,N'-ditert-butoxycarbonyl-7-(piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine

생성물 1

HCID 69696784N,N'-Di-tert-butoxycarbonyl-7-(1-benzylsulfonylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine수율 36.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N,N′-di-tert-butoxycarbonyl-7-(piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine (100 mg) in tetrahydrofuran (1.5 ml) were added pyridine (0.02 ml), 4-dimethylaminopyridine (12 mg) and α-toluenesulfonyl chloride (43 mg), and the mixture was stirred at room temperature for 12 hours and then at 50° C. for 6 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:acetone=3:1) and dried under reduced pressure to give the title compound (48 mg).

후처리

  1. waitat 50° C. for 6 hours
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:acetone=3:1)
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-dc810bceb2024c38980e3ca6770d8647
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562828B1

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