Methanol → 1-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383812노트

반응식

HRID 2383812 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH3:19])[C:9]2=[O:20])=[CH:4][C:3]=1[C:21](=[N:23][OH:24])[CH3:22].[H-].[Na+].CO>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:22][C:21]1[C:3]2[CH:4]=[C:5]([N:8]3[CH2:12][CH2:11][N:10]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][C:18]=4[CH3:19])[C:9]3=[O:20])[CH:6]=[CH:7][C:2]=2[O:24][N:23]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 866493961-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

생성물 1

HCID 498722501-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one수율 14.5%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매2회

실험 절차

1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (220 mg, 0.670 mmol) in DMF (5 mL) was added to a stirred mixture of NaH (19 mg, 0.804 mmol) in DMF (2 mL) under nitrogen atmosphere at 0° C. The resulting mixture was stirred at room temperature for 21 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and ice water. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 28 mg of the product (14.5% yield).

후처리

  1. customThe reaction mixture was partitioned between ethylacetate and ice water
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-6845d764a0294e1ba0fc8922f2518750
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263635B2

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