Triethylamine → N-{3-[5-(2-Methoxy-ethylamino)-6-(pyridine-3-carbonyl)-pyrazin-2-yl]phenyl}-acetamide

HRID 81461Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].Br[C:15]1[N:20]=[C:19]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=CN=2)=[O:22])[C:18]([NH:29][CH2:30][CH2:31][O:32][CH3:33])=[N:17][CH:16]=1.[CH2:34]([N:36](CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[CH3:33][O:32][CH2:31][CH2:30][NH:29][C:18]1[N:17]=[CH:16][C:15]([C:7]2[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=2)=[N:20][C:19]=1[C:21]([C:23]1[CH:34]=[N:36][CH:26]=[CH:27][CH:28]=1)=[O:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Palladium(II)acetate (2.83 mg, 0.006 mmol) and 1,1-bis(diphenylphosphino)ferrocene (5.42 mg, 0.0095 mmol) are dissolved in DMF (2 ml) and the mixture is stirred at 50° C. for 10 min. The mixture is cooled to room temperature and 3-acetamidobenzene boronic acid (25.5 mg, 0.14 mmol), [6-bromo-3-(2-methoxy-ethylamino)pyrazin-2-yl]pyridin-2-yl-methanone (Intermediate AC) (40 mg, 0.12 mmol) in DMF (1.5 ml) and triethylamine (24.9 μl, 0.18 mmol) are added. After stirring for 17 hours at 80° C. the solvent is removed in vacuo. Purification by flash chromatography eluting with CH2Cl2/MeOH, 98:2 affords the title compound. 1H NMR (DMSO-6) δ 10.0 (1H, s) 9.4 (1H, d), 8.9 (1H, t), 8.77-8.73 (1H, m), 8.4 (1H, dt), 8.1 (1H, s), 7.61-7.59 (1H, m), 7.54 (2H, t), 3.8-3.72 (2H, m), 3.62-3.56 (2H, m) 3.31 (3H, s) 2.02 (3H, s); MS m/z 376 [M+H]+

Workup

temperatureThe mixture is cooled to room temperature
stirringAfter stirring for 17 hours at 80° C. the solvent
customis removed in vacuo
customPurification by flash chromatography
washeluting with CH2Cl2/MeOH, 98:2

Sources & evidence

ORD record: ord-6da8d1e025c6478880d722f043d89a06
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846687B2

Reaction notes

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