Potassium Carbonate → N-(5-bicyclo-[2.2.1]heptanyl-methyl)-2-[3-(4-fluorophenyl)-propyl-sulfanyl]-pyridine-3-carboxylic acid amide

HRID 1925548ノート

反応式

HRID 1925548 の反応式
C([O-])([O-])=O.[K+].[K+].[CH:7]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[CH2:14][NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[SH:23].Br[CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1.CCCCCC.CC(=O)OCC>CN(C=O)C>[CH:10]12[CH2:13][CH:7]([CH:8]([CH2:14][NH:15][C:16]([C:17]3[C:18]([S:23][CH2:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:24])[CH2:9]1)[CH2:12][CH2:11]2

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 21226206Ethyl acetate hexaneHCID 178522760N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide

生成物 1

HCID 59487299N-(5-bicyclo-[2.2.1]heptanyl-methyl)-2-[3-(4-fluorophenyl)-propyl-sulfanyl]-pyridine-3-carboxylic acid amide収率 71%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

178 mg (1.29 mmol) of K2CO3 were added to a solution of 308 mg (1.18 mmol) of N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide in DMF (5 ml), and the mixture was stirred for 60 min at RT. 255 mg (1.18 mmol) of 1-(3-bromopropyl)-4-fluorobenzene were then added and the mixture was stirred for a further 16 h at RT. Dilution with water and extraction with EA were then carried out. The organic phase was washed with water, dried over MgSO4, filtered and concentrated in vacuo. CC (hexane/EA 2:1) of the residue yielded 333 mg (0.83 mmol, 71%) of N-(5-bicyclo-[2.2.1]heptanyl-methyl)-2-[3-(4-fluorophenyl)-propyl-sulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 399.2 [M+H]+.

後処理

  1. stirringthe mixture was stirred for a further 16 h at RT
  2. extractionDilution with water and extraction with EA
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-19dfaa88cfe14841ab9a31d7dba57701
出典データセット
uspto-grants-2012_05
特許番号
US08178684B2

反応ノート

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