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

HRID 490176

反応式

HRID 490176 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.[CH:16]1([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[C:25](=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]([CH2:25][NH:24][C:22]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:23])[CH2:12][CH:13]=1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 14283CyclohexanecarboxamideHCID 688728301',2',3',6'-Tetrahydro-2,4'-bipyridine hydrochloride

生成物 1

HCID 68872384N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)cyclohexanecarboxamide収率 64%

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), cyclohexanecarboxylic acid amide (64 mg, 0.5 mmol, Aldrich), 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 19 mg (64%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 1.19 (m, 4H), 1.26 (m, 2H), 1.61 (m, 1H), 1.68 (m, 3H), 2.18 (m, 1H), 2.55 (m, 2H), 2.68 (m, 2H), 3.18 (m, 2H), 4.02 (d, J=5 Hz, 2H), 6.68 (m, 1H), 7.22 (m, 1H), 7.52 (d, J=6 Hz, 1H), 7.73 (t, J=6 Hz, 1H), 8.02 (t, J=5 Hz, 1H), 8.52 (m, 1H); MS (ESI/APCI−) m/e 298 (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-3c91708860f2402382132a49cb1bde89
出典データセット
uspto-grants-2009_05
特許番号
US07528134B2

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