Triethylamine → Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester

HRID 1925001ノート

反応式

HRID 1925001 の反応式
[C:1]([O:5][C:6](=[O:32])[N:7]([C:22]1[C:23]2[N:24]([CH:29]=[CH:30][N:31]=2)[C:25]([Br:28])=[CH:26][N:27]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:10]([CH2:20][OH:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.C(OCC)(=O)C>[Br:28][C:25]1[N:24]2[CH:29]=[CH:30][N:31]=[C:23]2[C:22]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:32])[C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[C:10]([CH:9]=2)[CH2:20][O:21][S:41]([CH3:40])(=[O:43])=[O:42])=[N:27][CH:26]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86652629(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

生成物 1

HCID 86652630Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester収率 113.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a cooled solution (0° C.) of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.17 g, 0.34 mmol) in DCM (0.5 mL), is added triethylamine (0.104 mL, 0.74 mmol) followed by methanesulfonyl chloride (0.046 mL, 0.6 mmol). The reaction mixture is stirred at 0° C. for 1 hour and an additional hour at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.224 g) used in the next step without further purification.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-36ef034299b24abea3c5ee573131ebf2
出典データセット
uspto-grants-2012_05
特許番号
US08178530B2

反応ノート

読み込み中…