Dimethylformamide → 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2080276노트

반응식

HRID 2080276 반응식
Cl[C:2]1[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:5].[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[CH2:23][CH2:24][NH2:25].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Cl:18][C:16]1[CH:15]=[CH:14][C:3]([C:4]([NH:6][CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:5])=[C:2]([NH:25][CH2:24][CH2:23][C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([F:19])[CH:21]=2)[N:17]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5339282-(3-Fluorophenyl)ethanamineHCID 175874832,6-dichloro-N-(pyridin-3-ylmethyl)pyridine-3-carboxamide

생성물 1

HCID 597382236-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide수율 46%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 2,6-dichloro-N-(pyridin-3-ylmethyl)nicotinamide (20.4 g, 72.3 mmol), 3-fluorophenethyl amine (11.1 g, 79.5 mmol), K2CO3 (20 g 145 mmol) and DMF (200 mL) was stirred at 100° C. for 10 hours. The mixture was diluted with ethyl acetate (2×300 mL) and washed with saturated ammonium chloride, sodium bicarbonate and brine. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography to give 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (12.6 g, 46%). LRMS (M+H+) m/z 385.1.

후처리

  1. washwashed with saturated ammonium chloride, sodium bicarbonate and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-60903f7240f44134907988e09c2c190b
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932270B2

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