Methanol → HCID 59636198、化合物

HRID 80146

反応式

HRID 80146 の反応式
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

参加物

7

反応物 4

HCID 887Methanol2 回HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 866493992-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime

生成物 1

HCID 59636198HCID 59636198、化合物収率 70.4%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a43f94ed67a64d45848ca14060d1cedc
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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