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

HRID 2352923Notes

Reaction equation

HRID 2352923 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].[NH2:11][C:12]1[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=1)[C:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][C:22](=[O:26])[NH:23]2)=[CH:19][CH:18]=1)=[O:16]>C1COCC1>[O:26]=[C:22]1[CH2:21][C:20]2[C:24](=[CH:25][C:17]([C:15]([C:14]3[CH:13]=[C:12]([NH:11][C:8]([C:3]4[CH:4]=[N:5][N:6]([CH3:7])[C:2]=4[Cl:1])=[O:9])[CH:29]=[CH:28][CH:27]=3)=[O:16])=[CH:18][CH:19]=2)[NH:23]1

Participants

4

Reactant 2

HCID 27357735-Chloro-1-methyl-1H-pyrazole-4-carbonyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 866104235-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A dry flask was charged with 5-Chloro-1-methyl-1H-pyrazole-4-carbonyl chloride (0.200 g, 1.1 mmol) was dissolved in THF (10 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.178 g, 0.706 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for overnight. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was filtered. The solid residue was washed with 0° C. THF (10 mL) to afford the 5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a solid (0.199 g, 0.504 mmol, 71%).

Workup

  1. temperatureto reflux for overnight
  2. customThe room temperature reaction mixture
  3. filtrationwas filtered
  4. washThe solid residue was washed with 0° C

Sources & evidence

ORD record
ord-45f9bb5ec18145798dea85a255f2e76d
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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