Triethylamine → 6-bromo-N2-(5,7-difluoroquinolin-6-ylmethyl)pyrazine-2,3-diamine

HRID 1892426Notes

Reaction equation

[F:1][C:2]1[C:11]([CH2:12][NH2:13])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Br[C:16]1[C:17]([NH2:23])=[N:18][CH:19]=[C:20]([Br:22])[N:21]=1.C(N(CC)CC)C>CC#N>[Br:22][C:20]1[N:21]=[C:16]([NH:13][CH2:12][C:11]2[C:2]([F:1])=[C:3]3[C:8](=[CH:9][C:10]=2[F:14])[N:7]=[CH:6][CH:5]=[CH:4]3)[C:17]([NH2:23])=[N:18][CH:19]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of (5,7-difluoroquinolin-6-yl)methanamine (2.7 g, 13.9 mmol), 3,5-dibromopyrazin-2-amine (2.4 mg, 9.49 mmol) and triethyl amine (4.8 g, 47.5 mmol) in CH3CN (6 mL) was heated under microwave irradiation at 180° C. for 40 min. The reaction mixture was concentrated in vacuo and purified by column chromatography (hexane:EtOAc) to provide 6-bromo-N2-(5,7-difluoroquinolin-6-ylmethyl)pyrazine-2,3-diamine (1.50 g, 43%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.00 (d, 1H), 8.52 (d, 1H), 7.73 (d, 1H), 7.64 (m, 1H), 7.21 (s, 1H), 7.00 (s, 1H), 6.21 (s, 2H), 4.69 (d, 2H). LCMS (method B): [MH]+=367.9, tR=2.36 min

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by column chromatography (hexane:EtOAc)

Sources & evidence

ORD record: ord-cd54d4a2ec7f492cba0f2e23ad3496d6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

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