Dimethyl Sulfoxide → HCID 85789461, compound

HRID 392431Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:15][CH:14]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOCC>[CH:12]([C:13]1[CH:14]=[CH:15][C:16]([N:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[S:20]([CH2:23][CH3:24])(=[O:21])=[O:22])=[CH:17][CH:18]=1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of DMSO (0.190 mL, 2.68 mmol) in 4 mL DCM at −78° C. was added oxalyl chloride (0.146 mL, 1.67 mmol) dropwise. After 15 min a solution of N-(4-(hydoxymethyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (0.241 g, 0.669 mmol) was added via cannula. The reaction was stirred for 30 min and triethylamine (0.932 mL, 6.69 mmol) was added and warmed to 0° C. over 1 h. The mixture was poured into saturated NaHCO3 solution and diluted with ether. The organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel with 5:1 DCM/EtOAc to give 173 mg of a clear oil (72%). 1H NMR: 9.97 (s,1H), 8.50 (dd,J=4.9, 1.5 Hz, 1H), 8.35 (d,J=2.0 Hz, 1H), 7.87 (m,2H), 7.66 (dt,J=7.8, 2.0 Hz, 1H), 7.44 (m,2H), 7.24 (ddd,J=7.8, 4.9, 1.0 Hz, 1H), 4.97 (s,2H), 3.84 (q,J=9.3 Hz, 2H).

Workup

washThe organic layer was washed with H2O and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed on silica gel with 5:1 DCM/EtOAc

Sources & evidence

ORD record: ord-689ad00bb2c44df694fe971922fc8de3
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800651B2

Reaction notes

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