Pyruvic Acid → HCID 90039786, 화합물

HRID 526007노트

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HRID 526007 반응식
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.N12CCN(CC1)CC2.[NH2:15][C:16]1[C:25](I)=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:27])[N:17]=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[C:25]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:15][C:16]2=[N:17][C:18]=1[CH3:27])=[O:21]

참가 물질

6

반응물 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 59747893Methyl 6-amino-5-iodo-2-methylnicotinate

생성물 1

HCID 90039786HCID 90039786, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Under argon, pyruvic acid (6.90 ml, 100.1 mmol) and 1,4-diazabicyclo[2.2.2]octane (11.2 g, 100.1 mmol) were added to a solution of methyl 6-amino-5-iodo-2-methylnicotinate (9.00 g, 30.8 mmol) in N,N-dimethylformamide (88 ml), and the flask was evacuated and flushed with argon. Argon was subsequently passed through the solution for 5 min, palladium(II) acetate (0.345 g, 1.54 mmol) was then added and the mixture was heated at 100° C. for 2 h. The cooled solution was filtered through Celite and the dimethylformamide was distilled off. The residue was then taken up in water and acidified with hydrochloric acid, giving a solid (6.3 g, 86% of theory). HPLC-MS: log P=1.26; mass (m/z): 235.0 (M+H)+; 1H-NMR (DMSO) 2.79 (s, 3H), 3.85 (s, 3H), 7.19 (s, 1H), 8.62 (s, 1H), 12.50 (s, 1H).

후처리

  1. customthe flask was evacuated
  2. customflushed with argon
  3. filtrationThe cooled solution was filtered through Celite
  4. distillationthe dimethylformamide was distilled off
  5. customgiving a solid (6.3 g, 86% of theory)

출처 및 근거

ORD 기록
ord-9a619e9f2d914363960361d9b17d6462
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345247B2

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