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

HRID 1408413
Notes
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Reaction equation

HRID 1408413 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:15]=[CH:14][NH:13][N:12]=3)=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].Br[C:33]1[CH:34]=[CH:35][C:36]([Cl:45])=[C:37]([CH2:39][NH:40][C:41](=[O:44])[O:42][CH3:43])[CH:38]=1>O1CCOCC1.[Cu]I>[Cl:45][C:36]1[CH:35]=[CH:34][C:33]([N:13]2[CH:14]=[CH:15][C:11]([C:9]3[CH:8]=[CH:7][C:6]4[O:1][CH2:2][CH2:3][CH2:4][C:5]=4[CH:10]=3)=[N:12]2)=[CH:38][C:37]=1[CH2:39][NH:40][C:41](=[O:44])[O:42][CH3:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 15483918methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamateHCID 178419929HCID 178419929, compound2×

Product 1

HCID 67151156methyl N-[[2-chloro-5-[3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-1-yl]phenyl]methyl]carbamate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazole (i.e. the product of Step A) (600 mg, 3 mmol) in dioxane (50 mL) under nitrogen atmosphere, was added trans-N,N′-dimethylcyclohexane-1,2-diamine (86 mg, 0.6 mmol), followed by the addition of copper(I) iodide (114 mg, 0.6 mmol) and potassium carbonate (2.48 g, 18 mmol) to form a dark green-colored reaction mixture. To this reaction mixture was added methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamate (1.2 g, 4.5 mmol; prepared according to U.S. Pat. No. 6,313,071), and the reaction mixture was heated at 95° C. under nitrogen overnight. The reaction mixture was then concentrated and purified by silica gel column chromatography using 20% ethyl acetate in petroleum ether as eluant to provide the title product, a compound of the present invention, as a solid (110 mg).

Workup

  1. customto form a dark green-colored reaction mixture
  2. customprepared
  3. concentrationThe reaction mixture was then concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-5139c69f59ae42e8a972bfbcc085d912
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921360B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes