Triethylamine → N-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

HRID 2194986Notes

Reaction equation

HRID 2194986 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].[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[CH:20]([NH:22][CH:23]1[CH2:25][CH2:24]1)[CH2:19][CH2:18]2.C(N(CC)CC)C.CCCCCCC.C(OCC)(=O)C>O1CCCC1>[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[CH:20]([N:22]([CH:23]1[CH2:25][CH2:24]1)[C:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[F:1])=[O:10])[CH2:19][CH2:18]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108668795-Fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chlorideHCID 21899848Ethylacetate heptaneHCID 684283077-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 68429771N-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At ambient temperature, a solution of 0.19 g (1.06 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 3 ml of tetrahydrofurane is added dropwise to a solution of 0.20 g (0.96 mmol) of 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine and 0.15 ml triethylamine in 8 ml tetrahydrofurane. The reaction mixture is stirred for 3 hrs at reflux. The solvent is removed under vacuum and 10 ml of water are then added to the residue. The watery layer is extracted three times with ethyl acetate (3×20 ml); the combined organic layers are dried over magnesium sulphate and concentrated in vacuum. Column chromatography (gradient n-heptane/ethyl acetate) yields 0.26 mg (73% yield) of N-(7-chloro-2,3-dihydro-1H-inden-1-yl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide as an orange oil (M+1=348).

Workup

  1. temperatureat reflux
  2. customThe solvent is removed under vacuum and 10 ml of water
  3. additionare then added to the residue
  4. extractionThe watery layer is extracted three times with ethyl acetate (3×20 ml)
  5. dry with materialthe combined organic layers are dried over magnesium sulphate
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-2ae1423e97d042449efc25bcf4299670
Source dataset
uspto-grants-2012_12
Patent number
US08334390B2

Reaction notes

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