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Pyridine → Ethyl 1-{4-[(4-{[(tertbutoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 535908
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인쇄 미리보기

반응식

HRID 535908 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:25][C:26]1[N:31]=[CH:30][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][CH:27]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:31]3[C:26](=[O:25])[CH:27]=[CH:28][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30]3)=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1049PyridineHCID 86687861{4-[(4-{[(Tert-butoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}boronic acidHCID 178469094HCID 178469094, 화합물

생성물 1

HCID 86687860Ethyl 1-{4-[(4-{[(tertbutoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}-6-oxo-1,6-dihydropyridine-3-carboxylate

시약·촉매·용매 2

HCID 8895Cupric acetate촉매
HCID 6344
Dichloromethane
용매

실험 절차

A mixture of {4-[(4-{[(tert-butoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}boronic acid (800 mg; 2.39 mmol; prepared as described for the synthesis of intermediate X.7 without BOC deprotection step), ethyl 6-hydroxypyridine-3-carboxylate (420 mg; 2.51 mmol), copper(II) acetate (250 mg; 1.38 mmol) and pyridine (210 μl; 2.60 mmol) in DCM (10 ml) is stirred overnight. The mixture is filtered and extracted with water. The organic layer is dried with sodium sulphate, filtered and evaporated. The residue is purified by silica gel column chromatography (gradient DCM/methanol 98:2→94:4) to yield ethyl 1-{4-[(4-{[(tertbutoxy)carbonyl]amino}piperidin-1-yl)methyl]phenyl}-6-oxo-1,6-dihydropyridine-3-carboxylate

후처리

  1. customprepared
  2. filtrationThe mixture is filtered
  3. extractionextracted with water
  4. dry with materialThe organic layer is dried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by silica gel column chromatography (gradient DCM/methanol 98:2→94:4)

출처 및 근거

ORD 기록
ord-8e6902194cc849c494d57d7681896e95
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859559B2

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