1-tert-Butyl-5-methyl-1H-pyrazole-3-carbonyl chloride → HCID 86610441, compound

HRID 2352941Notes

Reaction equation

HRID 2352941 reaction equation
[C:1]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([C:11](Cl)=[O:12])=[N:6]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[CH:8]=[C:9]([CH3:10])[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N: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 27356831-tert-Butyl-5-methyl-1H-pyrazole-3-carbonyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 86610441HCID 86610441, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry flask was charged with 1-tert-Butyl-5-methyl-1H-pyrazole-3-carbonyl chloride (0.207 g, 1.032 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 1-tert-Butyl-5-methyl-1H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a solid (0.206 g, 0.490 mmol, 48%).

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-2355225309b0424fbe662c23355a8dbc
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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