碳酸钾 → 2-(2-(3-Cyanoindazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162759

反应方程式

HRID 1162759 反应方程式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([NH:22][C:23]1[S:27][C:26]2[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=2[C:24]=1[C:32]([NH2:34])=[O:33])=[O:21]>CN(C=O)C.O>[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:19][C:20]([NH:22][C:23]2[S:27][C:26]3[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=3[C:24]=2[C:32]([NH2:34])=[O:33])=[O:21])[N:2]=1)#[N:11]

参与物

6

反应物 3

HCID 11430碳酸钾HCID 4375561H-吲唑-3-甲腈HCID 595205232-(2-Bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

产物 1

HCID 595204552-(2-(3-Cyanoindazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide收率 14%

试剂、催化剂与溶剂 2

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

To a solution of 1H-indazole-3-carbonitrile (11 mg, 0.077 mmol) in DMF (500 μL) was added potassium carbonate and the whole was stirred at RT for 30 min before 2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (24 mg, 0.077 mmol) was added. The reaction mixture was heated to 60° C. and this temperature was maintained for 1.5 h before the reaction mixture was cooled to RT, then diluted with water (5 mL). The organics were extracted with diethyl ether (10 mL), EtOAc (10 mL) and DCM (10 mL), then combined and the suspension concentrated to dryness. The residue was dissolved in DMSO (1 mL) and purified by preparative reverse phase HPLC to give the title compound as a white solid (4 mg, 0.01 mmol, 14%).

后处理

  1. additionwas added
  2. temperaturethis temperature was maintained for 1.5 h before the reaction mixture
  3. temperaturewas cooled to RT
  4. extractionThe organics were extracted with diethyl ether (10 mL), EtOAc (10 mL) and DCM (10 mL)
  5. concentrationthe suspension concentrated to dryness
  6. dissolutionThe residue was dissolved in DMSO (1 mL)
  7. custompurified by preparative reverse phase HPLC

来源与证据

ORD记录
ord-5e422bed1d3342dd8738610cfc62d4ed
来源数据集
uspto-grants-2010_10
专利号
US07820707B2

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