Methyl iodide → Methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

HRID 528997ノート

反応式

HRID 528997 の反応式
[CH2:1]([N:5]([CH2:35][CH2:36][CH2:37][CH3:38])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[C:39]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CC(OC)(C)C>[CH2:35]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[N:11]([CH3:39])[CH:12]=1)=[O:7])[CH2:36][CH2:37][CH3:38]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178449064HCID 178449064、化合物

生成物 1

HCID 71062400Methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate収率 81.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

実験手順

To a stirred solution of methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (80 mg, 0.15 mmol) in dry DMF (3 mL) was added K2CO3 (42 mg, 0.30 mmol) and methyl iodide (22 mg, 0.15 mmol, a solution in 100 μL of DMF) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 4 h. The reaction mixture was diluted with MTBE and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo to give crude product. The crude material was purified by flash chromatography (gradient from 0% to 2% MeOH/CHCl3) to provide the title compound (65 mg, 79%). 1H NMR (CD3OD) δ 8.25-8.00 (m, 2H), 7.92-7.00 (m, 6H), 4.80-4.60 (m, 2H), 4.02 (s, 3H), 3.70-3.40 (m, 6H), 3.01 (s, 3H), 2.90-2.80 (m, 2H), 1.60-1.50 (m, 4H), 1.50-1.30 (m, 4H), 1.05-0.90 (m, 6H); MS(ESI+) m/z 531.4 (M+H)+.

後処理

  1. customat 0° C
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give crude product
  6. customThe crude material was purified by flash chromatography (gradient from 0% to 2% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-6b8e746646ca4bf491ac8449d465fdf9
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

反応ノート

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