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

HRID 80146노트

반응식

HRID 80146 반응식
F[C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[CH3:22])[C:12]2=[O:23])=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].[H-].[Na+].CO.C(Cl)Cl>CN(C=O)C.C(Cl)(Cl)Cl>[O:6]1[C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:21]=4[CH3:22])[C:12]3=[O:23])=[CH:7][C:3]=2[CH:4]=[N:5]1

참가 물질

7

반응물 4

HCID 887Methanol2회HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 866493992-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime

생성물 1

HCID 596361981-Benzo[d]isoxazol-5-yl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one수율 70.4%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매2회

실험 절차

2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime (I-113b:160 mg, 0.509 mmol) in dry DMF (2 mL) was added dropwise to a stirred mixture of NaH (72 mg, 1.52 mmol) in DMF (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 70 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The aqueous layer was distilled to afford the solid residue which was dissolved 1:1 DCM:MeOH. The crude product was purified by column chromatography on silica gel (4-5% MeOH in CHCl3). The residue was washed with hexane and dried to afford 105 mg of the product (70.4% yield).

후처리

  1. customThe reaction mixture was partitioned between ice water and ethylacetate
  2. distillationThe aqueous layer was distilled
  3. customto afford the solid residue which
  4. customThe crude product was purified by column chromatography on silica gel (4-5% MeOH in CHCl3)
  5. washThe residue was washed with hexane
  6. customdried

출처 및 근거

ORD 기록
ord-a43f94ed67a64d45848ca14060d1cedc
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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