Iodoethane → 1-{4-[(1-ethyl-1H-benzo[d]imidazol-2-yl)methyl]benzoyl}pyrrolidin-3-yl methanesulfonate

HRID 1163088ノート

反応式

HRID 1163088 の反応式
[CH3:1][S:2]([O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11](=[O:28])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:20]=3)=[CH:14][CH:13]=2)[CH2:7]1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH3:36]>CN(C=O)C>[CH3:1][S:2]([O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11](=[O:28])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[N:20]([CH2:35][CH3:36])[C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:14][CH:13]=2)[CH2:7]1)(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 866152161-(4-((1H-Benzo[d]imidazol-2-yl)methyl)benzoyl)pyrrolidin-3-yl Methanesulfonate

生成物 1

HCID 866152171-{4-[(1-ethyl-1H-benzo[d]imidazol-2-yl)methyl]benzoyl}pyrrolidin-3-yl methanesulfonate収率 19%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-5 °C

実験手順

A stirred solution of 1-{4-[(1H-benzo[d]imidazol-2-yl)methyl]benzoyl}-pyrrolidin-3-yl methanesulfonate (0.250 g, 0.6 mmol) in DMF was treated with potassium carbonate (0.260 g, 1.9 mmol), cooled to −5° C., treated dropwise with ethyl iodide (0.24 g, 1.5 mmol) at 0° C. over 20 min, warmed to room temperature, heated at 50° C. for 3 h, cooled to room temperature and filtered. The filtrate was concentrated in vacuo. The resultant residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate and concentrated in vacuo. Purification of this residue by column chromatography (neutral alumina, chloroform:methanol 100:0→98:2) afforded 1-{4-[(1-ethyl-1H-benzo[d]imidazol-2-yl)methyl]benzoyl}pyrrolidin-3-yl methanesulfonate (19%). 1H NMR (400 MHz, CDCl3): 7.79-7.77 (m, 1H), 7.44-7.51 (m, 3H), 7.32-7.25 (m, 4H), 5.37 & 5.23 (bs, 1H), 4.36 (s, 2H), 4.05-4.10 (q, J=8 Hz, 2H), 3.93 (bs, 1H), 3.82 (m, 1H), 3.57-3.71 (bs, 2H), 3.08 & 3.00 (s, 3H), 2.33-2.36 (m, 1H), 2.17-2.21 (m, 1H), 1.18-1.22 (t, J=8 Hz, 3H). [M+H] 428.

後処理

  1. temperaturewarmed to room temperature
  2. temperatureheated at 50° C. for 3 h
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionThe resultant residue was dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification of this residue by column chromatography (neutral alumina, chloroform:methanol 100:0→98:2)

出典と根拠

ORDレコード
ord-258b0575af254d32bd83840fe68e18e2
出典データセット
uspto-grants-2010_10
特許番号
US07820825B2

反応ノート

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