Isobutylamine → N-(isobutyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide

HRID 660064ノート

反応式

HRID 660064 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:34]([NH2:38])[CH:35]([CH3:37])[CH3:36]>C(Cl)Cl.C(OCC)(=O)C>[CH2:34]([NH:38][C:27](=[O:29])[C:26]1[CH:30]=[CH:31][CH:32]=[N:33][C:25]=1[S:24][CH2:23][CH2:22][S:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:20])=[O:21])[CH:35]([CH3:37])[CH3:36]

参加物

6

反応物 3

HCID 6558IsobutylamineHCID 682631,1'-CarbonyldiimidazoleHCID 28213502-[2-(Phenylsulfonyl)ethylthio]nicotinic acid

生成物 1

HCID 68745486N-(isobutyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

171 mg (1.05 mmol) of CDI were added to a solution of 323 mg (1.00 mmol) of 2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DCM (16 ml), and the mixture was stirred for 1 hour at RT. 99 μl (1.00 mmol) of isobutylamine were then added, and stirring was continued for a further 5 days at RT. The reaction solution was then washed in each case twice with a 4 M aq. ammonium chloride solution and a 1 M aq. sodium hydrogen carbonate solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue obtained was taken up in ethyl acetate (30 ml) and washed with 0.4 M hydrochloric acid (5 ml). The organic phase was again dried over MgSO4, filtered and concentrated in vacuo. 160 mg (0.42 mmol, 42 of N-(isobutyl)-2-(2-(phenylsulfonyl)ethylthio)nicotinamide were obtained as residue. MS: m/z 379.1 [M+H]+

後処理

  1. stirringstirring
  2. waitwas continued for a further 5 days at RT
  3. washThe reaction solution was then washed in each case twice with a 4 M aq. ammonium chloride solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. washwashed with 0.4 M hydrochloric acid (5 ml)
  9. dry with materialThe organic phase was again dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-376cee0168bb47cf8449a3967450de1e
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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