4-Chloro-1,3-dimethyl-1H-pyrazole-5-carbonyl chloride → HCID 86610402, compound

HRID 640945Notes

Reaction equation

HRID 640945 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[N:5][N:4]([CH3:8])[C:3]=1[C:9](Cl)=[O:10].OC=[C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([C:25]3[CH:26]=[C:27]([NH:31]C(=O)C)[CH:28]=[CH:29][CH:30]=3)=[O:24])=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:35]>C1COCC1>[O:35]=[C:15]1[CH2:14][C:22]2[C:17](=[CH:18][C:19]([C:23]([C:25]3[CH:26]=[C:27]([NH:31][C:9]([C:3]4[N:4]([CH3:8])[N:5]=[C:6]([CH3:7])[C:2]=4[Cl:1])=[O:10])[CH:28]=[CH:29][CH:30]=3)=[O:24])=[CH:20][CH:21]=2)[NH:16]1

Participants

4

Reactant 2

HCID 149958204-Chloro-1,3-dimethyl-1H-pyrazole-5-carbonyl chlorideHCID 178474162HCID 178474162, compound

Product 1

HCID 86610402HCID 86610402, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with 4-Chloro-2,5-dimethyl-2H-pyrazole-3-carbonyl chloride (0.152 g, 0.794 mmol) and THF (2 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.200 g, 0.794 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 4 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo. The tan solids were washed with THF (˜3 mL) and filtered to afford the pure 4-Chloro-2,5-dimethyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.187 g, 0.458 mmol, 58%).

Workup

  1. temperatureto reflux for 4 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. washThe tan solids were washed with THF (˜3 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e22ec001b6f54ab19fd74bbfd5039c7b
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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