Ethyl 2-chloroethanecarboximidate hydrochloride → tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate

HRID 1364077ノート

反応式

HRID 1364077 の反応式
[NH2:1][C:2]1[C:3]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][C:5]([CH3:21])=[C:6]([CH3:20])[C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].Cl.[Cl:30][CH2:31][C:32](=N)OCC>C(Cl)(Cl)Cl>[Cl:30][CH2:31][C:32]1[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]2[C:6]([CH3:20])=[C:5]([CH3:21])[N:4]=[C:3]([O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:2]=2[N:1]=1

参加物

4

反応物 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 21973822Tert-butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate

生成物 1

HCID 66957882tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate収率 115.7%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

反応条件

温度
60 °C

実験手順

tert-Butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate (68.8 g, 178 mmol), prepared as described in U.S. Pat. No. 6,545,016, Example 17, Parts A through C, was dissolved in chloroform (600 mL). Ethyl 2-chloroacetimidate hydrochloride (56.0 g, 354 mmol) was added to the solution and the reaction mixture was stirred at 60° C. for 72 hours. The reaction mixture was diluted with chloroform (200 mL), washed with brine (2×600 mL), and the layers were separated. The combined organics were dried over magnesium sulfate, filtered through CELITE filter aid, and concentrated under reduced pressure to afford 91.62 g of tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate.

後処理

  1. washwashed with brine (2×600 mL)
  2. customthe layers were separated
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered through CELITE
  5. filtrationfilter aid
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ba661bdab33b4c02933d9f590fea6437
出典データセット
uspto-grants-2011_02
特許番号
US07888349B2

反応ノート

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