Dimethyl Sulfoxide → HCID 57508940, compound

HRID 1665978Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:13]1[S:17][C:16]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=3)[N:19]=2)=[C:15]2[CH2:31][CH2:32][C:33]([CH3:36])([CH3:35])[CH2:34][C:14]=12)[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([C:13]1[S:17][C:16]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=3)[N:19]=2)=[C:15]2[CH2:31][CH2:32][C:33]([CH3:35])([CH3:36])[CH2:34][C:14]=12)[CH3:12]

Participants

Conditions

Temperature: -40 °C

Procedure

To a cold solution (−70° C.) of oxalyl chloride (169 mg, 1.34 mmol) and DMSO (209 mg, 2.67 mmol) in DCM (4 mL) a solution of {4-[5-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazol-3-yl]phenyl}-methanol (410 mg, 1.11 mmol) in DCM (5 mL) is added. The mixture is warmed to −40° C. within 30 min and then triethylamine (394 mg, 3.89 mmol) is added. Stirring is continued at −40° C. for 1 h, then at rt. The reaction is quenched by adding water and the mixture is extracted with diethyl ether. The organic extract is dried over MgSO4, filtered and the solvent of the filtrate is evaporated. The crude product is purified by chromatography on prep. TLC plates with heptane:EA 3:1 to give 4-[5-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazol-3-yl]-benzaldehyde (180 mg) as a white solid; LC-MS: tR=1.24 min, [M+1]+=367.24.

Workup

customat rt
customThe reaction is quenched
additionby adding water
extractionthe mixture is extracted with diethyl ether
extractionThe organic extract
dry with materialis dried over MgSO4
filtrationfiltered
customthe solvent of the filtrate is evaporated
customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record: ord-f13abe2a906a456ab4893905c1d22f23
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039644B2

Reaction notes

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