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1-Tert-butyl-4-isocyanatobenzene → N-(4-tert-butylphenyl)-3-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxamide

HRID 1246707
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HRID 1246707 반응식
[Cl:1][C:2]1[C:3]([N:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>ClCCl>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([N:15]2[CH:10]3[CH2:11][CH2:12][CH:13]2[CH2:14][N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:9]3)=[O:28])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]
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참가 물질

4

반응물 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 219047683-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

생성물 1

HCID 11463692N-(4-tert-butylphenyl)-3-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(3-Chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane (129 mg, 577 μmol) in dry dichloromethane (5 mL) was treated with 1-tert-butyl4-isocyanatobenzene (101 mg, 577 μmol) and allowed to stir overnight at room temperature. The mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (3:1, hexanes:ethyl acetate) to provide the title compound. MS (DCI/NH3) m/z: 399 (M+H)+; 1H NMR (CDCl3) δ 1.30 (s, 9H), 2.01 (m, 2H), 2.17 (m, 2H), 3.25 (d, 2H), 3.64 (dd, 2H), 4.38 (dd, 2H), 6.32 (s, 1H), 6.86 (dd, 1H), 7.32 (s, 4H), 7.59 (dd, 1H), 8.17 (dd, 1H).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (3:1, hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-3ed89a53f9d44dc79597729fdbb6a2b1
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07129235B2

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