Sodium hydride → 4-hydroxy-1-phenyl-3-(3-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one

HRID 217367

반응식

HRID 217367 반응식
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[H-].[Na+].[F:21][C:22]([F:34])([F:33])[C:23]1[CH:24]=[C:25]([CH2:29][C:30](Cl)=[O:31])[CH:26]=[CH:27][CH:28]=1>CN(C=O)C>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4](=[O:18])[C:3]=1[C:30](=[O:31])[CH2:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:33])([F:21])[F:34])[CH:24]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 127516363-(Trifluoromethyl)phenylacetyl chlorideHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

생성물 1

HCID 689473204-hydroxy-1-phenyl-3-(3-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In accordance with a process described in JP-61-246183A, 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one was synthesized. To a suspension of the synthesized compound (953 mg, 4.0 mmol) in DMF (32 mL) was added sodium hydride (purity of about 60%, 352 mg, 8.8 mmol, 2.2 eq.), and the mixture was stirred at a room temperature for 35 minutes. Then, 3-trifluoromethylphenylacetyl chloride (4.8 mmol, 1.2 eq.) was added thereto with cooling in an ice bath, and the mixture was stirred at a room temperature for 1.5 hours. Thereafter, the resulting mixture was purified by a flash column chromatography to give 4-hydroxy-1-phenyl-3-(3-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (1.04 g, yield 61%).

후처리

  1. customwas synthesized
  2. temperaturewith cooling in an ice bath
  3. stirringthe mixture was stirred at a room temperature for 1.5 hours
  4. customThereafter, the resulting mixture was purified by a flash column chromatography

출처 및 근거

ORD 기록
ord-4ddc99166d704e8d99bf3d4e2e64af1d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193356B2

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