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

HRID 640896Notes

Reaction equation

HRID 640896 reaction equation
[C:1]([N:5]1[C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]([CH3:13])=[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:10]([C:9]4[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]=[C:7]([CH3:13])[CH:8]=4)=[O:11])[CH:32]=[CH:31][CH:30]=3)=[O:19])=[CH:21][CH:22]=2)[NH:26]1

Participants

4

Reactant 2

HCID 27993401-tert-Butyl-3-methyl-1H-pyrazole-5-carbonyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 866103892-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 250 mL flask was charged with 2-tert-Butyl-5-methyl-2H-pyrazole-3-carbonyl chloride (1.00 g, 4.98 mmol) and THF (40 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 1.0 g, 3.96 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 3 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo. The solid residue was suspended in boiling EtOAc. The suspension was allowed to cool to room temperature before filtering to afford the 2-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a tan solid (0.984 g, 2.363 mmol, 60%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. temperatureto cool to room temperature
  5. filtrationbefore filtering

Sources & evidence

ORD record
ord-bfde56a3ad9f469f8a3ef885606f70d6
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

Loading…