Triethylamine → HCID 67508541, compound

HRID 1914918Notes

Reaction equation

HRID 1914918 reaction equation
[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8](Cl)=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1.[CH3:14][C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)[CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][NH:20]1.C(N(CC)CC)C>O1CCCC1>[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8]([N:20]2[CH2:21][CH2:22][CH2:23][CH:19]2[CH2:18][C:17]2[CH:24]=[CH:25][CH:26]=[C:15]([CH3:14])[CH:16]=2)=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 36140682-[(3-Methylphenyl)methyl]pyrrolidineHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chloride

Product 1

HCID 67508541HCID 67508541, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

At ambient temperature, a solution of 267 mg (1.25 mmol) of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride in 1 ml of tetrahydrofurane is added dropwise to a solution of 200 mg (1.14 mmol) of 2-(3-methylbenzyl)pyrrolidine and 127 mg (1.25 mmol) of triethylamine in 5 ml of tetra-hydrofurane. The reaction mixture is stirred for 1 hour at 70° C. The solvent is removed under vacuum and 100 ml of water are then added to the residue. The watery layer is extracted twice with ethyl acetate (2×150 ml) and the combined organic layers are successively washed by a 1 N solution of HCl, a saturated solution of potassium carbonate and filtered over a Chemelut™ cardridge to yield after concentration 350 mg of a beige oil. Column chromatography on silica gel (gradient heptane/ethyl acetate) yields 300 mg (71% yield) of [3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazol-4-yl][2-(3-methylbenzyl)pyrrolidin-1-yl]-methanone as a colourless oil (M+H=352).

Workup

  1. customThe solvent is removed under vacuum and 100 ml of water
  2. additionare then added to the residue
  3. extractionThe watery layer is extracted twice with ethyl acetate (2×150 ml)
  4. washthe combined organic layers are successively washed by a 1 N solution of HCl
  5. filtrationa saturated solution of potassium carbonate and filtered over a Chemelut™ cardridge
  6. customto yield after concentration 350 mg of a beige oil

Sources & evidence

ORD record
ord-3ea9076eaec34679a00e6290ac4b1265
Source dataset
uspto-grants-2013_12
Patent number
US08614242B2

Reaction notes

Loading…