Diisopropylethylamine → tert-Butyl 4-(5-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)pyridin-2-yl)piperazine-1-carboxylate

HRID 1021902Notes

Reaction equation

HRID 1021902 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Br[C:22]1[C:23](=[O:30])[N:24]([CH3:29])[CH:25]=[C:26]([Br:28])[N:27]=1.C(N(C(C)C)C(C)C)C>CC(O)C>[Br:28][C:26]1[N:27]=[C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)[C:23](=[O:30])[N:24]([CH3:29])[CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86684363tert-Butyl 4-(5-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)pyridin-2-yl)piperazine-1-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 197b (500 mg, 1.8 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (530 mg, 2.0 mmol), N-ethyl-N-isopropylpropan-2-amine (1.5 mL, 0.90 mmol), and propan-2-ol (20 mL) was stirred at 100° C. for 15 h. After the reaction was completed, the solvent was removed under reduced pressure to afford 197c as a brown solid (375 mg, 45%). MS-ESI: [M+H]+ 465.

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bb538e5ba8d246b5a16c27f1788dbe5c
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

Loading…