Triethylamine → HCID 22347523, 화합물

HRID 897148노트

반응식

HRID 897148 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2[N:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:3]1=2.[C:13](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:14].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2[N:8]=[C:9]([CH2:12][CH2:13][OH:14])[CH:10]=[CH:11][C:3]1=2

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 219345911,6-Dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

생성물 1

HCID 22347523HCID 22347523, 화합물수율 118.3%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1,6-dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (1.14 g, 7 mmol), di-tert-butyl dicarbonate (2.29 g, 10.5 mmol), DMAP (100 mg) and triethylamine (1.46 mL, 10.5 mmol) in 30 mL THF was refluxed 72 hours under N2. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate. The mixture was washed with brine, dried over Na2SO4. After filtration and concentration at reduced pressure, the crude mixture was purified by flash chromatography on silica gel (40% EA/Hex) to afford the desired product (1.6 g, 90% yield) as yellow oil. H NMR (400 MHz, CDCl3) δ 1.51 (s, 9H), 2.40 (s, 3H), 2.90 (s, 3H), 3.28 (t, 2H), 3.83 (m, 2H), 6.78 (d, 1H), 6.83(d, 2H). Step 6. Synthesis of tert-butyl 6-(2-ethoxy-2-oxoethyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate.

후처리

  1. washThe mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration at reduced pressure
  4. customthe crude mixture was purified by flash chromatography on silica gel (40% EA/Hex)

출처 및 근거

ORD 기록
ord-5eb9df62633047c9a11865c62c4e596a
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921767B2

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