Triethylamine → HCID 68650403, 화합물

HRID 646679노트

반응식

HRID 646679 반응식
[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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 131728097HCID 131728097, 화합물

생성물 1

HCID 68650403HCID 68650403, 화합물수율 70.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-24bd5747960f4881977ab8dfc11619a4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

반응 노트

불러오는 중…