异喹啉羧酸 → Ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate

HRID 1372719

反应方程式

HRID 1372719 反应方程式
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][C:16]=1[Br:27].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Br:27][C:16]1[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:15]=1[NH:14][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1)=[O:13]

参与物

8

反应物 4

HCID 68092异喹啉羧酸HCID 757711-羟基苯并三唑(HOBT)HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 19702145Ethyl 2-(4-amino-3-bromophenyl)acetate

产物 1

HCID 58778618Ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate收率 69%

试剂、催化剂与溶剂 3

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
60 °C

实验过程

In DMF (15 ml) were dissolved 1-isoquinolinecarboxylic acid (1.00 g, 5.77 mmol), ethyl 4-amino-3-bromophenylacetate (1.49 g, 5.77 mmol), HOBt (0.39 g, 2.89 mmol), and DMAP (0.14 g, 1.15 mmol). To the resulting solution was added EDC HCl (1.33 g, 6.93 mmol). After stirring at 60° C. for 5 hours, the reaction mixture was cooled to room temperature. Water was added, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane:ethyl acetate (4:1, v/v) eluate fractions, ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate (1.64 g, 69%) was obtained as a yellow solid.

后处理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane:ethyl acetate (4:1

来源与证据

ORD记录
ord-4f6477460f244b1295b64770b1c2e833
来源数据集
uspto-grants-2007_01
专利号
US07157487B2

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