1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54671227, compound

HRID 869046Notes

Reaction equation

Br[C:2]1[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[N:7]=1.[C:21]([C:23]1[N:28]=[C:27]([NH2:29])[CH:26]=[CH:25][CH:24]=1)#[CH:22].C1CCN2C(=NCCC2)CC1>C(#N)C.[Pd]>[NH2:29][C:27]1[N:28]=[C:23]([C:21]#[C:22][C:2]2[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=3)[N:7]=2)[CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (75 mg, 0.2105 mmol), 6-ethynylpyridin-2-amine (29.84 mg, 0.2526 mmol), Pd EnCat 30 (33.68 mg, 0.01347 mmol) and DBU (70.50 mg, 69.25 μL, 0.4631 mmol) were combined in acetonitrile (1.500 mL). The reaction mixture was heated at 100° C. under microwave conditions for 1.5 hours. After this time the solid residue was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether to 10% MeOH/DCM) to give the titled product as a beige solid (21 mg, 26% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.45 (sept, 1H), 6.20 (s, 2H), 6.52 (d, 1H), 7.06 (d, 1H), 7.07 (br s, 2H), 7.45 (dd, 1H), 7.90 (d, 2H), 8.25 (d, 2H) and 8.78 (s, 1H) ppm; MS (ES+) 394.1.

Workup

customAfter this time the solid residue was removed by filtration
concentrationthe filtrate concentrated in vacuo
customThe residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-6991d3d164384fbd9565a982b34f6c2b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969356B2

Reaction notes

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