Sodium Bicarbonate → Tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate

HRID 1668649ノート

反応式

HRID 1668649 の反応式
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)=[C:2]=[O:3].C([O-])(O)=O.[Na+].[NH2:16][C:17]1[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=1)[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1>CCOC(C)=O>[CH3:10][C:7]1[N:8]=[CH:9][C:4]([NH:1][C:2](=[O:3])[NH:16][C:17]2[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=2)[CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:26][CH2:27]2)=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 73305055-Isocyanato-2-methylpyridineHCID 57597088Tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate2 回

生成物 1

HCID 57597105Tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate収率 63%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%).

後処理

  1. customThe resulting reaction mixture
  2. customthe layers were separated
  3. washThe organic layer was washed twice with saturated aq. NaHCO3 and once with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant

出典と根拠

ORDレコード
ord-dfce87d29410485b9d3088855995598e
出典データセット
uspto-grants-2011_08
特許番号
US07989455B2

反応ノート

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