Hydrochloric Acid → 4-Sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile

HRID 85545노트

반응식

HRID 85545 반응식
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][CH:14]([CH2:20][CH3:21])/[CH:15]=[CH:16]/[C:17](=O)[CH3:18].NCC1C(=O)NC(C)=CC=1CCC.O=O.Cl>CS(C)=O.O>[CH:14]([C:15]1[CH:16]=[C:17]([CH3:18])[NH:12][C:10](=[O:11])[C:9]=1[C:7]#[N:8])([CH2:20][CH3:21])[CH3:13]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 977OxygenHCID 7898CyanoacetamideHCID 53645545-Methyl-3-hepten-2-oneHCID 23665647Potassium tert-butoxide2회HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate

생성물 1

HCID 682102564-Sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile수율 53%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a stirred solution of t-BuOK (8 g, 71.42 mmol) and cyanoacetamide (6.6 g, 78.57 mmol) in DMSO (80 mL) was added (E)-5-methylhept-3-en-2-one, 2 (9 g, 71.42 mmol) under argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for 1 h and then added additional t-BuOK (24 g, 214.28 mmol) was added. Then argon was displaced by oxygen and stirred at RT for 48 h. The reaction mixture was cooled to 0° C., diluted with water (36 mL) followed by 4N HCl (up to pH˜4) and the resulting reaction mixture was stirred for 15 min. The separated solid was collected by filtration, washed with water (10 mL), pet ether (100 mL) and dried to afford the title compound as yellow solid (7 g, 53%). 1H NMR (DMSO-d6, 400 MHz): δ 0.816-0.779 (t, 3H, J=7.6 Hz), 1.178-1.161 (d, 3H, J=6.8 Hz), 1637-1.505 (m, 2H), 2.24 (s, 3H), 2.814-2.760 (m, 1H), 6.239 (s, 1H), 12.324 (bs, 1H); LCMS (ES−) m/z=189.20 (M−H)

후처리

  1. additionwas added
  2. stirringstirred at RT for 48 h
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customthe resulting reaction mixture
  5. stirringwas stirred for 15 min
  6. filtrationThe separated solid was collected by filtration
  7. washwashed with water (10 mL), pet ether (100 mL)
  8. customdried

출처 및 근거

ORD 기록
ord-bdf06db785e841b8aa4c462587de416a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846935B2

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