Triethylamine → HCID 72234673, compound

HRID 1916021Notes

Reaction equation

HRID 1916021 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([F:24])[CH2:22][CH:21]2[NH2:23])=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2([F:24])[CH2:22][CH:21]2[NH:23][C:8]([C:7]2[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=2)=[O:9])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 44398212HCID 44398212, compound

Product 1

HCID 72234673HCID 72234673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.105 g; 0.54 mmol) in dichloromethane (2 ml) was added dropwise to a stirred solution of the amine from example P5 (compound Z1.004; 2-(4-chlorophenyl)-2-fluoro-cyclopropylamine; 0.100 g; 0.54 mmol) and triethylamine (0.15 ml; 1.08 mmol) in dichloromethane (3 ml). The reaction mixture was stirred for 1 hr at ambient temperature then allowed to stand for 18 h. The reaction mixture was washed with 2M HCl (5 ml) and with saturated NaHCO3 (5 ml) and then dried over MgSO4. Evaporation of the solvent yielded 0.15 g 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-(4-chlorophenyl)-2-fluoro-cyclopropyl)-amide in the form of a yellow solid (81% of theory) as a 7:3 mixture of cis/trans isomers.

Workup

  1. waitto stand for 18 h
  2. washThe reaction mixture was washed with 2M HCl (5 ml) and with saturated NaHCO3 (5 ml)
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-511df9176ae24a6dacfb1bcbfa38833f
Source dataset
uspto-grants-2013_12
Patent number
US08618023B2

Reaction notes

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