1-Tert-butyl-4-isocyanatobenzene → HCID 11292477, compound

HRID 1394083Notes

Reaction equation

HRID 1394083 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:13]3[CH2:14][CH2:15][CH:9]2[CH2:10][NH:11][CH2:12]3)=[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:11]2[CH2:12][CH:13]3[N:8]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=4)[CH:9]([CH2:15][CH2:14]3)[CH2:10]2)=[O:28])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 219047698-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

Product 1

HCID 11292477HCID 11292477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-(3-Chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane (102 mg, 456 μmol) and 1-tert-butyl-4-isocyanatobenzene (80 mg, 456 μmol) were combined in dry dichloromethane (4.5 mL) and stirred overnight at room temperature. The mixture was concentrated and the residue was purified by chromatography on silica gel (7:3, hexanes:ethyl acetate) to provide the title compound. MS (ESI) m/z: 399 (M+H)+; 1H NMR (DMSO-d6) δ 1.25 (s, 9H), 1.73 (m, 2H), 1.85 (m, 2H), 3.20 (dd, 2H), 3.92 (dd, 2H), 4.51 (dd, 2H), 6.94 (dd, 1H), 7.24 (d, 2H), 7.37 (d, 2H), 7.79 (dd, 1H), 8.17 (dd, 1H), 8.30 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel (7:3, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-484cd0454c1f42de98b8fbf936237f2f
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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