Formic Acid → HCID 68587830, 화합물

HRID 406604노트

반응식

HRID 406604 반응식
[CH3:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14].[OH-].[Na+].C(O)=O>CO>[CH3:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:14])([F:15])[F:16]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 67251895Methyl 4-methyl-5-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 68587830HCID 68587830, 화합물수율 83.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 4-methyl-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate (1.4 g, 4.9 mmol) was dissolved in methanol (12 mL), and a 5 M aqueous sodium hydroxide solution (10 mL) was added thereto, and the resulting mixture was heated under reflux for 3 hours. After the mixture was cooled to room temperature, formic acid (5 mL) was added thereto to stop the reaction. After the mixture was concentrated under reduced pressure, water (10 mL) was added thereto to suspend the resulting residue. The precipitated solid was collected by filtration and washed 3 times with water. The obtained solid was dried under reduced pressure, whereby 4-methyl-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylic acid (1.1 g, 83%) was obtained as a solid. The thus obtained solid was suspended in dichloromethane (10 mL), oxalyl chloride (0.86 mL, 10 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 2 hours. After the mixture was concentrated under reduced pressure, the residue was dissolved in tetrahydrofuran (10 mL), and 4-(methylsulfonyl)aniline hydrochloride (1.0 g, 4.9 mmol) and N,N-diisopropylethylamine (2.8 mL, 16 mmol) were sequentially added to the solution, and the resulting mixture was heated under reflux for 18 hours. After the mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and acetonitrile (10 mL) and 3 M hydrochloric acid (100 mL) were added to the residue. A precipitated solid was triturated, collected by filtration and washed with water, and then, dried under reduced pressure, whereby 4-methyl-N-[4-(methylsulfonyl) phenyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxamide (1.4 g, 89%) was obtained as a solid.

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customthe reaction
  4. concentrationAfter the mixture was concentrated under reduced pressure, water (10 mL)
  5. additionwas added
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed 3 times with water
  8. customThe obtained solid was dried under reduced pressure

출처 및 근거

ORD 기록
ord-b19c431fd8a2427aad09ecd6d699c096
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754118B2

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