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

HRID 490175

반응식

HRID 490175 반응식
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.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH2:22])=[O:21].[C:26](=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH:22][CH2:26][N:11]1[CH2:10][CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH2:13][CH2:12]1)=[O:21]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 692543-ChlorobenzamideHCID 688728301',2',3',6'-Tetrahydro-2,4'-bipyridine hydrochloride

생성물 1

HCID 688764323-chloro-N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)benzamide수율 61%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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-chlorobenzamide (78 mg, 0.5 mmol, Lancaster), 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 20 mg (61%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 2.58 (m, 2H), 2.79 (t, J=4 Hz, 2H), 3.30 (m, 2H), 4.30 (d, J=5 Hz, 2H), 6.71 (m, 1H), 7.22 (m, 1H), 7.52 (m, 2H), 7.62 (d, J=6 Hz, 1H), 7.73 (t, J=6 Hz, 1H), 7.85 (d, J=6 Hz, 1H), 7.92 (s, 1H), 8.52 (m, 1H), 9.08 (t, J=5 Hz, 1H); MS (ESI/APCI−) m/e 326 (M−H)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c05a05324a24037bdf3321ea14c7281
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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