Triethylamine → HCID 22347523、化合物

HRID 897148ノート

反応式

HRID 897148 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 22347523HCID 22347523、化合物収率 118.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5eb9df62633047c9a11865c62c4e596a
出典データセット
uspto-grants-2005_07
特許番号
US06921767B2

反応ノート

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