Triethylamine → HCID 25054438, compound

HRID 1716443Notes

Reaction equation

HRID 1716443 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].[CH:12]1([NH:15][CH:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH2:17][CH3:18])[CH2:14][CH2:13]1.C(N(CC)CC)C.ClCCl.CO>ClCCl>[CH:12]1([N:15]([CH:16]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH2:17][CH3:18])[C:9]([C:3]2[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=2[F:1])=[O:10])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108668795-Fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chlorideHCID 21226129Dichloromethane methanolHCID 68683092HCID 68683092, compound

Product 1

HCID 25054438HCID 25054438, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At ambient temperature a solution of 0.16 g (0.93 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 2 ml of dichloromethane was added dropwise to a solution of 0.15 g (0.85 mmol) of N-cyclopropyl-1-pyridin-4-yl-propylamine and 0.14 ml of triethylamine in 5 ml of dichloromethane. The reaction mixture was stirred for 12 hrs at ambient temperature and then at 40° C. for 8 hrs and washed with water. The organic layers were filtrated over basic alumina and dried. Column chromatography (gradient dichloromethane/Methanol) yielded 0.18 mg (44% yield) of N-cyclopropyl-N-[1-pyridin-4-yl-propyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (M+H=317).

Workup

  1. waitat 40° C. for 8 hrs
  2. washwashed with water
  3. filtrationThe organic layers were filtrated over basic alumina
  4. customdried

Sources & evidence

ORD record
ord-f724acdae5ff4b3db1bea7faf0240367
Source dataset
uspto-grants-2010_09
Patent number
US07803821B2

Reaction notes

Loading…