Formaldehyde → N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)-3,5-dimethylbenzamide

HRID 490180

反応式

HRID 490180 の反応式
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=1.C=O.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[C:20]([NH2:22])=[O:21].[C:27](=O)([O-])[O-].[K+].[K+]>C(O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:9][CH2:10][N:11]([CH2:27][NH:22][C:20](=[O:21])[C:19]2[CH:23]=[C:24]([CH3:26])[CH:25]=[C:17]([CH3:16])[CH:18]=2)[CH2:12][CH:13]=1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 3194853,5-DimethylbenzamideHCID 688728301',2',3',6'-Tetrahydro-2,4'-bipyridine hydrochloride

生成物 1

HCID 68873067N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)-3,5-dimethylbenzamide収率 56%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl hydrochloride (20 mg, 0.10 mmol, Saari, W. S.; et al. J. Med. Chem. 1984, 27, 1182), paraformaldehyde (30 mg, 1 mmol), 3,5-dimethylbenzamide (75 mg, 0.5 mmol), and 42 mg of potassium carbonate (0.3 mmol) in 2.5 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 18 mg (56%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ2.33 (s, 6H), 2.56 (m, 2H), 2.78 (t, J=4 Hz, 2H), 3.28 (m, 2H), 4.18 (d, J=5 Hz, 2H), 6.71 (m, 1H), 7.18 (s, 1H), 7.22 (m, 1H), 7.50 (m, 3H), 7.75 (t, J=6 Hz, 1H), 8.52 (d, J=5 Hz, 1H), 8.62 (t, J=5 Hz, 1H), MS (ESI/APCI−) m/e 320 (M−H)+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen overnight
  3. filtrationfiltered
  4. customthe solvent was removed
  5. customThe residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

出典と根拠

ORDレコード
ord-beb57b0b56f84f2a97d28998edf34501
出典データセット
uspto-grants-2009_05
特許番号
US07528134B2

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