Potassium Carbonate → methyl N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate

HRID 1408427Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:17])[O-:16].[CH3:18]N[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].I[C:35]1[CH:36]=[CH:37][C:38]2[O:43][CH2:42][CH2:41][CH2:40][C:39]=2[CH:44]=1>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:35]3[CH:36]=[CH:37][C:38]4[O:43][CH2:42][CH2:41][CH2:40][C:39]=4[CH:44]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:16])[O:17][CH3:18]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of methyl N-[[(2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (prepared according to a procedure described in World Patent Publication WO 2008/124092) (600 mg, 2.2 mmol) in dioxane (60 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (60 mg, 0.452 mmol) under nitrogen atmosphere. Then copper(I) iodide (86 mg, 0.452 mmol) and potassium carbonate (1.87 g, 13.5 mmol) were added to form a dark-green-colored reaction mixture. To the reaction mixture was added 3,4-dihydro-6-iodo-2H-1-benzopyran (882 mg, 3.39 mmol). The reaction mixture was heated at 95° C. under nitrogen overnight, the solvent was evaporated, and the residue was purified by silica gel column chromatography (30% ethyl acetate/petroleum ether as eluant) to provide the title product, a compound of the present invention, as solid (0.318 g).

Workup

customto form a dark-green-colored reaction mixture
customthe solvent was evaporated
customthe residue was purified by silica gel column chromatography (30% ethyl acetate/petroleum ether as eluant)

Sources & evidence

ORD record: ord-5b4537b09ea2414b86422a8a8bf2bda8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921360B2

Reaction notes

Loading…