1,1'-Carbonyldiimidazole → HCID 86686311, compound

HRID 1043871Notes

Reaction equation

HRID 1043871 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[N:11]=[CH:10][C:9]=2[C:18]([OH:20])=O)=[C:4]([Cl:21])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:34][O:35][C:36]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:37]=1[CH2:38][NH2:39].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[N:11]=[CH:10][C:9]=2[C:18]([NH:39][CH2:38][C:37]2[CH:40]=[CH:41][C:42]([O:44][CH3:45])=[CH:43][C:36]=2[O:35][CH3:34])=[O:20])=[C:4]([Cl:21])[CH:3]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 86686309HCID 86686309, compound

Product 1

HCID 86686311HCID 86686311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-5-(4-bromo-2-chlorophenyl)-1-(tetrahydrofuran-3-yl)-1H-pyrazole-4-carboxylic acid (1 g) was dissolved in DCM (20 mL), and CDI (611 mg) was added, followed by stirring at room temperature for one hour. 2,4-dimethoxybenzylamine (0.809 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for two hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with DCM. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 40%) to give the title compound (1.26 g).

Workup

  1. stirringthe mixture was stirred at room temperature for two hours
  2. extractionfollowed by extraction with DCM
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 40%)

Sources & evidence

ORD record
ord-3f2cf96a1ea9491999aee8e7c4a9ad2b
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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