2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride → 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 640862Notes

Reaction equation

HRID 640862 reaction equation
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]([CH3:10])=[N:3]1.[NH2:11][C:12]1[CH:29]=[CH:28][C:15]([C:16]([C:18]2[CH:26]=[C:25]3[C:21]([CH2:22][C:23](=[O:27])[NH:24]3)=[CH:20][CH:19]=2)=[O:17])=[CH:14][CH:13]=1>C1COCC1>[O:27]=[C:23]1[CH2:22][C:21]2[C:25](=[CH:26][C:18]([C:16]([C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH:5]=4)=[O:8])=[CH:29][CH:28]=3)=[O:17])=[CH:19][CH:20]=2)[NH:24]1

Participants

4

Reactant 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 592564856-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 866103832,5-Dimethyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with 2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride (0.820 g, 5.15 mmol) and THF (10 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 15, 1.00 g, 3.97 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, and the crude residue was dissolved in EtOH (5 mL). The ethanolic solution was treated with 1M NaOH(aq) (2 mL) and stirred for 30 min. The basic solution was acidified to a pH of 1 with 1M HCl(aq) yielding a tan precipitate. The solids were filtered to afford the pure 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (1.35 g, 3.60 mmol, 91%).

Workup

  1. temperatureto reflux for 4 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionthe crude residue was dissolved in EtOH (5 mL)
  5. additionThe ethanolic solution was treated with 1M NaOH(aq) (2 mL)
  6. customyielding a tan precipitate
  7. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-b5b5fd5473484a96b9ce0eb83ed4a300
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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