Methanol → 1-[4-(Cyclopropyl-hydroxy-methyl)-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383893

반응식

HRID 2383893 반응식
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[F:6][C:7]1[CH:14]=[C:13]([N:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:25]=3[CH3:26])[C:16]2=[O:27])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].CO>C1COCC1.C(Cl)(Cl)Cl>[CH:1]1([CH:9]([OH:10])[C:8]2[CH:11]=[CH:12][C:13]([N:15]3[CH2:19][CH2:18][N:17]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][C:25]=4[CH3:26])[C:16]3=[O:27])=[CH:14][C:7]=2[F:6])[CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 887MethanolHCID 596361642-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehydeHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 596361411-[4-(Cyclopropyl-hydroxy-methyl)-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one수율 99.41%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A 0.5M solution of cyclopropyl magnesium bromide in THF (2.4 mL, 1.170 mmol) was added dropwise to 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-121a: 175 mg, 0.585 mmol) in dry THF (10 mL) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was quenched with aqueous NH4Cl solution and the THF layer was concentrated. The aqueous layer was extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (3% MeOH in CHCl3), followed by hexane wash, afforded 200 mg of the product (99.41% yield).

후처리

  1. customThe reaction mixture was quenched with aqueous NH4Cl solution
  2. concentrationthe THF layer was concentrated
  3. extractionThe aqueous layer was extracted with ethylacetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (3% MeOH in CHCl3)
  8. washwash

출처 및 근거

ORD 기록
ord-dc741ca648e14b3fba759eff055bf800
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263635B2

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