Hydrogen Peroxide → 1-[(2,3-dichlorophenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxamide

HRID 44491ノート

反応式

HRID 44491 の反応式
[OH-:1].[K+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][N:12]1[C:16]2[CH:17]=[C:18]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:19]=[C:20]([C:21]#[N:22])[C:15]=2[N:14]=[C:13]1[CH3:29].OO>O.C1COCC1>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][N:12]1[C:16]2[CH:17]=[C:18]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[CH:19]=[C:20]([C:21]([NH2:22])=[O:1])[C:15]=2[N:14]=[C:13]1[CH3:29]

参加物

6

反応物 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 569596841-[(2,3-dichlorophenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carbonitrile

生成物 1

HCID 569596811-[(2,3-dichlorophenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxamide収率 51.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A solution of KOH (78 mg, 1.4 mmol) in water (10 mL) was added dropwise to solution of 1-[(2,3-dichlorophenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carbonitrile (280 mg, 0.7 mmol) and 30% H2O2 (3 mL) in THF (10 mL) at rt. The mixture was heated at 50° C. for 2 h. When TLC showed no starting material left, the pH of the mixture was acidified to pH ca. 5 and extracted with EtOAc (50 mL×3). The organic layer was washed with brine, dried over MgSO4, concentrated. The resulting residue was purified by silica gel chromatography eluted with EtOAc to give the product (150 mg, 51%), as a white solid. 1H NMR (300 Mhz, DMSO-d6) δ ppm 2.44 (s, 3H), 3.11 (t, 4H, J=4.8 Hz), 3.71 (t, 4H, J=4.8 Hz), 5.60 (s, 2H), 6.31 (d, 1H, J=8.1 Hz), 7.16 (br s, 2H), 7.25 (t, 1H, J=8.1 Hz), 7.35 (d, 1H, J=1.8 Hz), 7.41 (d, 1H, J=1.8 Hz), 7.60 (d, 1H, J=8.1 Hz); LC-MS: m/e=419 [M+1]+

後処理

  1. waitleft
  2. extractionextracted with EtOAc (50 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography
  7. washeluted with EtOAc

出典と根拠

ORDレコード
ord-14527f1f18e44baf8a800fb929cade17
出典データセット
uspto-grants-2013_09
特許番号
US08541411B2

反応ノート

読み込み中…