HCID 86662073, compound → 1-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanone

HRID 1959377Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:19](N(OC)C)=[O:20])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[CH3:25][Mg+].[Br-]>C1COCC1>[NH2:1][C:2]1[C:3]([C:19](=[O:20])[CH3:25])=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:6][N:7]=1

Participants

Conditions

Temperature: -20 °C

Procedure

3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamide (864 mg, 2.411 mmol) was dissolved in THF (10 mL) and cooled to −20° C. under nitrogen. MeMgBr (2.411 mL of 3 M, 7.233 mmol) was added dropwise and the reaction was left to stir at this temperature for 15 minutes after which time the reaction was allowed to slowly warm to ambient temperature. A further MeMgBr (803.7 μL of 3 M, 2.411 mmol) was added and analysis showed after 10 minutes showed no SM remaining. The mixture was quenched with 10 mL 1M HCl, stirred for 5 mins and then extracted with EtOAc (3×), dried (MgSO4), filtered and the solvent removed in vacuo to give the product as an orange solid (510 mg, 68% Yield). 1H NMR (400.0 MHz, DMSO) d 1.23 (t, 3H), 2.54 (s, 3H), 3.11 (q, 2H), 3.30-3.32 (m, 4H), 3.47-3.49 (m, 4H), 7.42 (br s, 2H) and 8.34 (s, 1H) ppm; MS (ES+) 314.0

Workup

waitthe reaction was left
temperatureto slowly warm to ambient temperature
waitanalysis showed after 10 minutes
customThe mixture was quenched with 10 mL 1M HCl
stirringstirred for 5 mins
extractionextracted with EtOAc (3×)
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-fb7aebee5f5f401fa508a56a30160da8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

Loading…