海萝胶 → 1-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester

HRID 907535

反应方程式

HRID 907535 反应方程式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:12][C:13]1[C:17](Cl)=[N:16][S:15][N:14]=1.Cl>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:17]2[C:13]([Cl:12])=[N:14][S:15][N:16]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参与物

5

反应物 3

HCID 313海萝胶HCID 707704-哌啶甲酸乙酯HCID 798043,4-二氯-1,2,5-噻二唑

产物 1

HCID 590139411-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester收率 106.2%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

Piperidine-4-carboxylic acid ethyl ester (14.0 mL, 91 mmol) was dissolved in DMF (15.0 mL) and heated to 100 C. 3,4-Dichloro-1,2,5-thiadiazole (4.0 mL, 42 mmol) was added and the mixture heated at 100 C. for 4 h. The reaction mixture was poured into 1N HCl and extracted with EtOAc (4×). The combined EtOAc extractions were washed with H2O (1×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give 12.3 g (105%) of 1-(4-chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester which was used without further purification. 1H NMR (CDCl3) 4.30-4.13 (m, 2H), 4.06-3.93 (m, 2H), 3.12-2.99 (m, 2H), 2.59 (m, 1H), 2.03 (m, 4H), 1.42-1.26 (m, (3H) ppm. LC-MS (MH+)=276.

后处理

  1. temperatureheated to 100 C
  2. temperaturethe mixture heated at 100 C
  3. extractionextracted with EtOAc (4×)
  4. extractionThe combined EtOAc extractions
  5. washwere washed with H2O (1×), sat'd NaCl (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-c005bf9eda2847f994da754bc05b8427
来源数据集
uspto-grants-2011_09
专利号
US08013156B2

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