2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride → HCID 86610411, compound

HRID 2352895Notes

Reaction equation

HRID 2352895 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:13]=[C:14]([CH:26]=[CH:27][CH:28]=1)[CH2:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][C:21](=[O:25])[NH:22]2)=[CH:18][CH:17]=1>C1COCC1>[O:25]=[C:21]1[CH2:20][C:19]2[C:23](=[CH:24][C:16]([CH2:15][C:14]3[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:28]=[CH:27][CH:26]=3)=[CH:17][CH:18]=2)[NH:22]1

Participants

4

Reactant 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 68700636HCID 68700636, compound

Product 1

HCID 86610411HCID 86610411, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with 2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride (0.146 g, 0.924 mmol) and THF (2 mL). 6-(3-Amino-benzyl)-1,3-dihydro-indol-2-one (as prepared in Example 91, 0.200 g, 0.840 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, and the crude residue was dissolved in EtOH (2 mL). The ethanolic solution was treated with 1M NaOH(aq) (1 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 precipitate that formed was filtered and washed with THF (˜2 mL) affording the 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indol-6-ylmethyl)-phenyl]-amide (0.115 g, 0.319 mmol, 38%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionthe crude residue was dissolved in EtOH (2 mL)
  5. additionThe ethanolic solution was treated with 1M NaOH(aq) (1 mL)
  6. customyielding a tan precipitate
  7. customThe precipitate that formed
  8. filtrationwas filtered
  9. washwashed with THF (˜2 mL)

Sources & evidence

ORD record
ord-5849eaabcd39483a86eb8b35e7a30d78
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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