Oxalyl chloride → HCID 67345378, compound

HRID 1673527Notes

Reaction equation

HRID 1673527 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[CH:17]=[C:16]([C:18]([OH:20])=O)[NH:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:21][C:22]1[CH:34]=[C:33]([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:32]=[CH:31][C:23]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[CH2:35]([C:33]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[C:22]([NH:21][C:18]([C:16]2[NH:15][N:14]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:17]=2)=[O:20])[CH:34]=1)[CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 121025Pyrazole-5-carboxylic acid, 3-phenyl-HCID 516892Sodium BicarbonateHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 67345378HCID 67345378, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.0 mL of methylene chloride, 2.7 μL of N,N-dimethylformamide and 0.061 mL of oxalyl chloride were sequentially added to 0.13 g of 3-phenyl-1H-pyrazole-5-carboxylic acid at room temperature and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 3.0 mL of methylene chloride and 0.45 mL of triethylamine containing 60 mg of tert-butyl 2-amino-4-phenethylbenzoate at room temperature was stirred at the same temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4.1] to obtain tert-butyl 4-phenethyl-2-(3-phenyl-1H-pyrazole-5-carboxamido)benzoate.

Workup

  1. stirringwas stirred at the same temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4.1]

Sources & evidence

ORD record
ord-55630a1b7b1345fbab3282a28e6fdbe7
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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