1,2-Dichloroethane → HCID 59580759, compound

HRID 1470419Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([N:13]([CH3:20])[C:14](=[O:19])[CH2:15][CH2:16][S:17][CH3:18])=[CH:11][N:12]=2)[CH:5]=[N:6][CH:7]=1.B1([O-])O[O:22]1.O.O.O.O.[Na+].C([O-])(O)=O.[Na+].ClCCCl>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([N:13]([CH3:20])[C:14](=[O:19])[CH2:15][CH2:16][S:17]([CH3:18])=[O:22])=[CH:11][N:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To N-[2-(5-fluoro-pyridin-3-yl)-thiazol-5-yl]-N-methyl-3-methylsulfanyl-propionamide (Compound 30, 44 mg, 0.14 mmol) in glacial acetic acid (1.5 mL) was added sodium perborate tetrahydrate (23 mg, 0.14 mmol), and the mixture was heated at 65° C. for 2 h. The reaction mixture was carefully poured into a separatory funnel containing saturated aqueous NaHCO3 resulting in gas evolution. When the gas evolution had ceased, DCE was added and the layers were separated. The aqueous layer was extracted twice with DCE, and all the organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to give the desired product as white solid (20 mg, 45%): mp 152-154° C.; 1H NMR (300 MHz, CDCl3) δ 8.95 (s, 1H), 8.59 (s, 0.3H), 8.49 (s, 0.7H), 7.98 (d, J=9.3 Hz, 1H), 7.73 (s, 0.3H), 7.62 (s, 0.7H), 3.64 (s, 2.1H), 3.36 (s, 0.9H), 3.40-2.70 (m, 4H), 2.69 (s, 2.1H), 2.61 (s, 0.9H); ESIMS m/z 328.1 (M+1), m/z 326.1 (M−1).

Workup

additionThe reaction mixture was carefully poured into a separatory funnel
customthe layers were separated
extractionThe aqueous layer was extracted twice with DCE
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b8292813a938449983b73ee37e9b2f9c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006446B2

Reaction notes

Loading…