N-(3-cyanopyridin-2-yl)-N-methylmethanesulfonamide → N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide

HRID 472388ノート

反応式

HRID 472388 の反応式
[C:1]([C:3]1[C:4]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>[Pd].N.CO>[NH2:2][CH2:1][C:3]1[C:4]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 2

HCID 12568879N-(3-cyanopyridin-2-yl)-N-methylmethanesulfonamideHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 45480403N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 222Ammonia溶媒HCID 887Methanol溶媒

実験手順

N-(3-Aminomethyl-pyridin-2-yl)-N-methyl-methanesulfonamide was prepared from N-(3-cyano-pyridin-2-yl)-N-methyl-methanesulfonamide (3.35 g, 15.8 mmol) (prepared as described in J. Heterocyclic Chemistry, 1979, 16, 1361-1363) via hydrogenation using a Paar apparatus with 10% palladium on carbon (50% Wet) (5:45:50, Palladium:carbon black:Water, 5.71 g, 2.68 mmol) and hydrogen (50 psi) in 7M ammonia in methanol (100 mL). The mixture was shaken on a Paar apparatus until adsorption of hydrogen ceased. The mixture was degassed, backflushed with nitrogen, filtered through a plug of diatomaceous earth and rinsed with dichloromethane. The filtrate was evaporated under reduced pressure. Product isolated as pale yellow oil (3.20, 93%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.37 (dd, J=4.6, 1.7 Hz, 1H), 7.92 (dd, J=7.7, 1.7 Hz, 1H), 7.32 (dd, J=7.7, 4.8 Hz, 1H), 4.04 (s, 2H), 3.26 (s, 3H), 3.08 (s, 3H). MS=216 (MH)+.

後処理

  1. customThe mixture was degassed
  2. filtrationfiltered through a plug of diatomaceous earth
  3. washrinsed with dichloromethane
  4. customThe filtrate was evaporated under reduced pressure
  5. customProduct isolated as pale yellow oil (3.20, 93%)

出典と根拠

ORDレコード
ord-7c256a008c8a4137813c565becbdeff8
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

反応ノート

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