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

HRID 1246707Notes

Reaction equation

HRID 1246707 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3ed89a53f9d44dc79597729fdbb6a2b1
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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