1,2-Dichloroethane → HCID 59580759, compound

HRID 533312Notes

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-0677b2701312472b9edbb1a42d7f8922
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853246B2

Reaction notes

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