3-(Tert-Butyl)-1-Methyl-1H-Pyrazole-5-Carbonyl Chloride → 5-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 641020Notes

Reaction equation

HRID 641020 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11](Cl)=[O:12])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[C:18]([C:20]1[CH:28]=[C:27]2[C:23]([CH2:24][C:25](=[O:29])[NH:26]2)=[CH:22][CH:21]=1)=[O:19]>C1COCC1>[O:29]=[C:25]1[CH2:24][C:23]2[C:27](=[CH:28][C:20]([C:18]([C:17]3[CH:16]=[C:15]([NH:14][C:11]([C:7]4[N:8]([CH3:10])[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=4)=[O:12])[CH:32]=[CH:31][CH:30]=3)=[O:19])=[CH:21][CH:22]=2)[NH:26]1

Participants

4

Reactant 2

HCID 27356843-(Tert-Butyl)-1-Methyl-1H-Pyrazole-5-Carbonyl ChlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 866104525-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry flask was charged with 5-tert-Butyl-2-methyl-2H-pyrazole-3-carbonyl chloride (0.207 g, 1.03 mmol) and THF (10 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.260 g, 1.03 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux overnight. The reaction mixture was then allowed to cool to room temperature and subsequently vacuum filtered. The solid was washed with 0° C. THF (˜5 mL) and collected to afford the 5-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a solid (0.390 g, 0.94 mmol, 91%).

Workup

  1. temperatureto reflux overnight
  2. filtrationsubsequently vacuum filtered
  3. washThe solid was washed with 0° C
  4. customTHF (˜5 mL) and collected

Sources & evidence

ORD record
ord-e87e75ef39b145368d8393cbbf3129fd
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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