1-Phenyl-1H-pyrazole-5-carbonyl chloride → HCID 86610433, compound

HRID 641004Notes

Reaction equation

HRID 641004 reaction equation
[C:1]1([N:7]2[C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[C:19]([C:21]1[CH:29]=[C:28]2[C:24]([CH2:25][C:26](=[O:30])[NH:27]2)=[CH:23][CH:22]=1)=[O:20]>C1COCC1>[O:30]=[C:26]1[CH2:25][C:24]2[C:28](=[CH:29][C:21]([C:19]([C:18]3[CH:17]=[C:16]([NH:15][C:12]([C:11]4[N:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[N:8]=[CH:9][CH:10]=4)=[O:13])[CH:33]=[CH:32][CH:31]=3)=[O:20])=[CH:22][CH:23]=2)[NH:27]1

Participants

4

Reactant 2

HCID 27765651-Phenyl-1H-pyrazole-5-carbonyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 86610433HCID 86610433, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry flask was charged with 2-Phenyl-2H-pyrazole-3-carbonyl chloride (0.164 g, 0.794 mmol) and THF (8 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.200 g, 0.793 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 2-Phenyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a solid (0.255 g, 0.600 mmol, 76%).

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-8a7ac6e4d6924dab8d95b54c8f1d521a
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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