4-Methoxybenzyl alcohol → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-methoxybenzyl)oxy)pyridin-2(1H)-one

HRID 2202917ノート

反応式

HRID 2202917 の反応式
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]O)=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:30][C:27]5[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=5)=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 77384-Methoxybenzyl alcoholHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 896910841-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

生成物 1

HCID 896910601-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-methoxybenzyl)oxy)pyridin-2(1H)-one収率 31.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg), (4-methoxy-phenyl)-methanol (98 mg) and tributylphosphine (320 μl) in THF (10 ml) was added 1,1′-(azodicarbonyl)dipiperidine (269 mg). The mixture was stirred under sonication at 50° C. for 1 h. The reaction mixture was then cooled to room temperature, and concentrated in vacuo. The crude residue was diluted with DCM (100 ml), and the DCM layer was washed with water (50 ml) and brine (30 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (45 mg) as an off-white solid.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe crude residue was diluted with DCM (100 ml)
  4. washthe DCM layer was washed with water (50 ml) and brine (30 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

出典と根拠

ORDレコード
ord-2088f12bac0e46c587230b586f55c002
出典データセット
uspto-grants-2016_06
特許番号
US09365540B2

反応ノート

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