m-Chloroperbenzoic acid → HCID 59471806, compound

HRID 78617Notes

Reaction equation

[CH:1]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([C:18]2[O:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:21][N:22]=2)[C:14]([NH2:17])=[N:15][CH:16]=1)([CH3:3])[CH3:2].ClC1C=C(C(OO)=[O:37])C=CC=1>ClCCl>[CH:1]([S:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([C:18]2[O:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:21][N:22]=2)[C:14]([NH2:17])=[N:15][CH:16]=1)=[O:37])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

5-(2-isopropylsulfanylphenyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (50 mg, 0.1284 mmol) was dissolved in dichloromethane (10 mL) and cooled to 0° C. in an ice-bath. 3-Chlorobenzenecarboperoxoic acid (26.59 mg, 0.1541 mmol) was added in one portion with rapid stirring. The mixture was stirred at 0° C. for 15 min, washed with saturated aqueous NaHCO3 solution (1×5 mL) and brine (1×5 mL), dried over MgSO4 and concentrated in vacuo to leave a solid which was purified by column chromatography on silica eluting with ether/ petroleum ether to yield the product as a yellow solid (16.1 mg, 31% yield); 1H NMR (400.0 MHz, CDCl3) d 1.2 (d, 3H), 1.35 (d, 3H), 3.5-3.6 (m, 1H), 7.5-7.75 (m, 2H), 7.5-7.65 (m, 7H), 8.25 (d, 2H) and 8.55 (s, 1H) ppm; MS (ES+) 406.1

Workup

washwashed with saturated aqueous NaHCO3 solution (1×5 mL) and brine (1×5 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto leave a solid which
customwas purified by column chromatography on silica eluting with ether/ petroleum ether

Sources & evidence

ORD record: ord-e50146d7ef714483af87c8aeeaa99fd3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841308B2

Reaction notes

Loading…