Triethylamine → N-cyclopropyl-N-[(3,4-dimethoxypyridin-2-yl)methyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

HRID 1716441Notes

Reaction equation

HRID 1716441 reaction equation
[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9](Cl)=[O:10].[CH3:12][O:13][C:14]1[C:15]([CH2:22][NH:23][CH:24]2[CH2:26][CH2:25]2)=[N:16][CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C(N(CC)CC)C.CCCCC.C(OCC)(=O)C>ClCCl>[CH:24]1([N:23]([CH2:22][C:15]2[C:14]([O:13][CH3:12])=[C:19]([O:20][CH3:21])[CH:18]=[CH:17][N:16]=2)[C:9]([C:3]2[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=2[F:1])=[O:10])[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108668795-Fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chlorideHCID 22335286Ethyl acetate pentaneHCID 67072906N-[(3,4-dimethoxypyridin-2-yl)methyl]cyclopropylamine

Product 1

HCID 25054439N-cyclopropyl-N-[(3,4-dimethoxypyridin-2-yl)methyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At ambient temperature a solution of 0.14 g (0.8 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 2 ml of dichloromethane was added drop wise to a solution of 0.15 g (0.7 mmol) of N-[(3,4-dimethoxypyridin-2-yl)methyl]cyclopropylamine and 0.3 ml of triethylamine in 4 ml of dichloromethane. The reaction mixture was stirred for 16 hrs at ambient temperature and quenched with water. The watery layer was extracted three times with dichloromethane (3×10 ml), the combined organic layers were dried over magnesium sulphate and concentrated in vacuum. Column chromatography (gradient n-pentane/ethyl acetate) yielded 0.23 mg (92% yield) of N-cyclopropyl-N-[(3,4-dimethoxypyridin-2-yl)methyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (M+H=349).

Workup

  1. customquenched with water
  2. extractionThe watery layer was extracted three times with dichloromethane (3×10 ml)
  3. dry with materialthe combined organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-d3b5690e42874de485c090ad4c159dce
Source dataset
uspto-grants-2010_09
Patent number
US07803821B2

Reaction notes

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