Tetrahydrofuran → HCID 57786364、化合物

HRID 1399325ノート

反応式

HRID 1399325 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24](OC)=[O:25])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]21.[CH:28]1([Mg]Br)[CH2:30][CH2:29]1.[Cl-].[NH4+].O1[CH2:39][CH2:38][CH2:37]C1>>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=4[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([C:24]([CH:37]2[CH2:38][CH2:39]2)([CH:28]2[CH2:30][CH2:29]2)[OH:25])=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 57785965HCID 57785965、化合物HCID 178418630HCID 178418630、化合物

生成物 1

HCID 57786364HCID 57786364、化合物収率 52%

反応条件

温度
50 °C

実験手順

To a solution of methyl 9-chloro-1-(2-chloro-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (100 mg, 0.246 mmol) in tetrahydrofuran (2.5 mL) was added a solution of cyclopropyl magnesium bromide in tetrahydrofuran (1.0 M, 1.5 mL, 1.5 mmol) at 0° C. The mixture was stirred at room temperature for 0.5 hr and at 50° C. for 1 hr. Aqueous ammonium chloride was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/n-hexane to give the title compound (58.6 mg, 0.128 mmol, 52%) as colorless crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-f13833534e7e49d7ba2ef9e2f330081c
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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