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

HRID 1394079Notes

Reaction equation

HRID 1394079 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-butyl-4-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-6e939479ff1440d3bd6c2133eb3e25c5
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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