Triethylamine → HCID 68650403, compound

HRID 646679Notes

Reaction equation

HRID 646679 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 68650403HCID 68650403, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-24bd5747960f4881977ab8dfc11619a4
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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