Triethylamine → HCID 68650403、化合物

HRID 646679ノート

反応式

HRID 646679 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5](Br)=[CH:6][N:7]=1.CC[C:11]([NH2:13])=[O:12].[C:14]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)([O:16][CH3:17])=[O:15].[CH2:27](N(CC)CC)[CH3:28]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:22]2[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=2)[C:14]([O:16][CH3:17])=[O:15])=[N:4][C:3]=1[C:11]([NH:13][CH2:27][CH3:28])=[O:12]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 131728097HCID 131728097、化合物

生成物 1

HCID 68650403HCID 68650403、化合物収率 70.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-amino-6-bromopyrazine-2-ethylcarboxamide (5.0 g, 20.4 mmol), [1,1′bis-(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (0.93 g, 2.04 mmol), 3-carbomethoxyphenylboronic acid (4.4 g, 24.4 mmol) in DMF (30 mL) was de-gassed with nitrogen. Triethylamine (5.7 mL, 40.1 mmol) was then added and the resulting mixture was heated at 85° for 2.5 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL), filtered over silica gel, washed with saturated sodium bicarbonate solution (150 mL), dried over sodium sulfate, filtered, and concentrated. The oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield) to give methyl 3-{5-amino-6-[(ethylamino)carbonyl]pyrazin-2-yl}benzoate (4.3 g, 70% yield): 1H NMR (400 MHz, CDCl3): 8.66 (s, 1H), 8.53-8.52 (t, 1H), 8.08-8.06 (m, 2H), 8.00 (b, 1H), 3.5 (t, 1H), 3.97 (s, 3H), 2.91-2.88 (m, 1H), 0.94-0.85 (m, 2H), 0.72-0.62 (m, 2H); MS (EI) for C15H16N4O3: 301 (MH+).

後処理

  1. customwas de-gassed with nitrogen
  2. temperaturethe resulting mixture was heated at 85° for 2.5 hours
  3. filtrationfiltered over silica gel
  4. washwashed with saturated sodium bicarbonate solution (150 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield)

出典と根拠

ORDレコード
ord-24bd5747960f4881977ab8dfc11619a4
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

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