(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester → Benzyl-{4-[3-(5-cyano-pyrazin-2-yl)-ureido]-3-methoxy-benzyl}-carbamic acid tert-butyl ester

HRID 1019754ノート

反応式

HRID 1019754 の反応式
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]([C:28]1[N:29]=[CH:30][C:31]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)=[N:32][CH:33]=1)#[N:27]>CN(C=O)C>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:35]([NH:34][C:31]2[CH:30]=[N:29][C:28]([C:26]#[N:27])=[CH:33][N:32]=2)=[O:36])=[C:18]([O:23][CH3:24])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 21034184(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl esterHCID 22064357Phenyl 5-cyanopyrazin-2-ylcarbamate

生成物 1

HCID 67469180Benzyl-{4-[3-(5-cyano-pyrazin-2-yl)-ureido]-3-methoxy-benzyl}-carbamic acid tert-butyl ester収率 67.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester (0.25 g, 0.73 mmol) and phenyl 5-cyanopyrazin-2-ylcarbamate (0.21 g 0.87 mmol) (Example 10) were dissolved in DMF (2.5 mL) and heated at 80° C. for 2 hours. The mixture was allowed to cool to room temperature then partitioned between water (15 mL) and EtOAc (25 mL). The separated aqueous layer was extracted with EtOAC (25 ml), and then the combined organic extracts were washed with water (15 mL), brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane to afford the title compound (0.24 g, 67%).

後処理

  1. temperatureto cool to room temperature
  2. customthen partitioned between water (15 mL) and EtOAc (25 mL)
  3. extractionThe separated aqueous layer was extracted with EtOAC (25 ml)
  4. washthe combined organic extracts were washed with water (15 mL), brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane

出典と根拠

ORDレコード
ord-f15812e27e2e479c84682c7fa7e02bc8
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

読み込み中…