Triethylamine → 2-[2-(3-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide

HRID 660060ノート

反応式

HRID 660060 の反応式
[F:1][C:2]1[CH:3]=[C:4]([S:8]([CH2:11][CH2:12]O)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.CS(Cl)(=O)=O.C([O-])([O-])=O.[K+].[K+].[SH:32][C:33]1[N:47]=[CH:46][CH:45]=[CH:44][C:34]=1[C:35]([NH:37][CH2:38][C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)=[O:36]>C(Cl)Cl.CN(C=O)C.CC(=O)OCC.C(Cl)Cl.CC(=O)OCC>[F:1][C:2]1[CH:3]=[C:4]([S:8]([CH2:11][CH2:12][S:32][C:33]2[N:47]=[CH:46][CH:45]=[CH:44][C:34]=2[C:35]([NH:37][CH2:38][C:39]2[S:40][CH:41]=[CH:42][CH:43]=2)=[O:36])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

参加物

10

反応物 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 27591433-FluorophenylsulfonylethanolHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

生成物 1

HCID 687272312-[2-(3-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide収率 22%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

A solution of 408 mg (2.0 mmol) of 2-(3-fluorophenylsulfonyl)ethanol in DCM (5 ml) was cooled to 0° C.; 304 μl (2.2 mmol) of NEt3 and 154 μl (2.0 mmol) of methanesulfonic acid chloride were added thereto, and stirring was carried out for 16 hours at RT. In another vessel, 275 mg (2.0 mmol) of K2CO3 were added to a solution of 500 mg (2.0 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide in DMF (6 ml), and stirring was carried out for 30 min at RT. The DCM reaction solution was added to this solution, and stirring was continued for 72 hours at RT. The mixture was then diluted with EA and washed with 1 N aqueous NaHCO3 solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC (DCM/EA 4:1) of the residue yielded 194 mg (0.44 mmol, 22%) of 2-[2-(3-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide. MS: m/z 437.0 [M+H]+

後処理

  1. stirringstirring
  2. waitwas carried out for 30 min at RT
  3. additionwas added to this solution
  4. stirringstirring
  5. waitwas continued for 72 hours at RT
  6. washwashed with 1 N aqueous NaHCO3 solution
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ffb0c654c7f44716a0a34aa0f4cb972c
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

反応ノート

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