Ethyl Acetate → HCID 118045562, compound

HRID 595883Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[N:12][C:11]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])C(OC(C)(C)C)=O)=[CH:10][N:9]=1)(=O)=O.[CH3:29][S-:30].[Na+].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:29][S:30][CH2:6][CH2:7][C:8]1[N:9]=[CH:10][C:11]([NH:14][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[N:12][CH:13]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To 2-(5-(bis(tert-butoxycarbonyl)amino)pyrazin-2-yl)ethyl methanesulfonate (540 mg, 1.293 mmol) in DMF (7 mL) was added sodium thiomethoxide (408 mg, 5.82 mmol) and was stirred at 85° C. for 3 h, followed by LCMS. The reaction was let cool, 200 mL of ethyl acetate and saturated sodium bicarbonate was added. The organic layer was extracted and washed water (3×), saturated salt solution, dried sodium sulfate, filtered through 2 cm silica gel plug and flushed with ethyl acetate. The solvent was concentrated off to constant mass to give 294 mg of the desired product as free base used as is, (84% yield). LCMS (m/z): 270.4 (MH+), 0.84 min. 1H NMR (400 MHz, CDCl3) δ ppm 9.19 (s, 1H), 8.08 (d, J=1.2 Hz, 1H), 7.20 (br. s., 1H), 2.99-3.08 (m, 2H), 2.79-2.94 (m, 2H), 2.12 (s, 3H), 1.54 (s, 9H).

Workup

temperatureThe reaction was let cool
extractionThe organic layer was extracted
washwashed water (3×), saturated salt solution, dried sodium sulfate
filtrationfiltered through 2 cm silica gel plug
customflushed with ethyl acetate
concentrationThe solvent was concentrated off to constant mass

Sources & evidence

ORD record: ord-655dcd26dd324c81a349c1e8be630eca
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

Loading…