Triethylamine → HCID 10111963, compound

HRID 227583Notes

Reaction equation

HRID 227583 reaction equation
CS(Cl)(=O)=O.[Cl:6][C:7]1[CH:11]=[C:10]([C:12]([OH:14])=O)[N:9]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[N:8]=1.[CH2:22]([N:24](CC)CC)C.[Na+].[NH2:30][C:31]1[C:32]([C:38]([O-:40])=O)=[N:33][CH:34]=[N:35][C:36]=1[CH3:37]>C(#N)C.O>[Cl:6][C:7]1[CH:11]=[C:10]([C:12]([NH:30][C:31]2[C:32]([C:38]([NH:24][CH3:22])=[O:40])=[N:33][CH:34]=[N:35][C:36]=2[CH3:37])=[O:14])[N:9]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[N:8]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 211073323-Chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acidHCID 67181984HCID 67181984, compound

Product 1

HCID 10111963HCID 10111963, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 0.26 mL (3.3 mmol) of methanesulfonyl chloride in 18 mL of acetonitrile at 0° C. was added 0.77 g (3.0 mmol) of 3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxylic acid from Step J. 0.42 mL (3.0 mmol) of triethylamine in 9 mL of acetonitrile was added dropwise. After 20 minutes at 0° C., 0.525 g (3.0 mmol) of material from Step F was added. After 15 minutes 0.42 mL (3.0 mmol) of triethylamine was added dropwise. After 2 hours 0.26 mL (3.3 mmol) of methanesulfonyl chloride was added. After stirring overnight. The reaction mixture was poured into water. Filtration afforded 0.27 g of the title compound.

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-660867e722d8439dac520a236d594069
Source dataset
uspto-grants-2009_07
Patent number
US07560564B2

Reaction notes

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