Water → HCID 86679335, compound

HRID 1464908Notes

Reaction equation

HRID 1464908 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:10]=1[O:11][CH2:12][CH2:13][NH:14][CH:15]1[CH2:17][CH2:16]1.[F:23][CH:24]([F:35])[C:25]1[C:29]([C:30](Cl)=[O:31])=[C:28]([F:33])[N:27]([CH3:34])[N:26]=1.O>ClCCl>[CH:15]1([N:14]([CH2:13][CH2:12][O:11][C:10]2[C:9]([Cl:8])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:22])[C:30]([C:29]2[C:25]([CH:24]([F:35])[F:23])=[N:26][N:27]([CH3:34])[C:28]=2[F:33])=[O:31])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 60687263HCID 60687263, compound

Product 1

HCID 86679335HCID 86679335, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 13 ml Chemspeed™ vial is weighted 73 mg (0.726 mmol) of triethylamine. Then 3 ml of a 0.23 molar solution of N-[2-(2,6-dichlorophenoxy)ethyl]cyclopropanamine (0.594 mmole) in dichloromethane is added followed by 3 ml of a 0.26 molar solution of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride (0.66 mmole) in dichloromethane and stirred at ambient temperature for 15 hrs. 1 ml of water is then added and the mixture is deposited on a basic alumina cartridge (2 g) and eluted twice by 8 ml of dichloromethane. The solvents are removed to yield 183 mg (64%) of pure N-cyclopropyl-N-[2-(2,6-dichlorophenoxy)ethyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide as an oil (M+H=422).

Workup

  1. washeluted twice by 8 ml of dichloromethane
  2. customThe solvents are removed

Sources & evidence

ORD record
ord-996dc535dfa24fb39b60c410b4a7e819
Source dataset
uspto-grants-2015_04
Patent number
US08999956B2

Reaction notes

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