Dichloromethane → HCID 136149986, compound

HRID 2263411Notes

Reaction equation

[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:6][C:7]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19](=[O:21])[O:18][N:17]=2)=[C:12]([O:22][CH3:23])[CH:11]=1.ClCCl>CN(C)C=O.[O-2].[O-2].[Mn+4]>[CH3:23][O:22][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[C:16]1[NH:20][C:19](=[O:21])[O:18][N:17]=1)[O:9][CH2:8][C:7]1[S:6][C:5]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)=[N:4][C:3]=1[CH:2]=[O:1]

Participants

Conditions

Temperature: 60 °C

Procedure

50 mg of 3-{4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one were dissolved in 2 mL of dimethylformamide by heating to 60° C. and 2 mL of dichloromethane was added. To the resulting solution was added 90 mg of manganese dioxide. The reaction mixture was heated to 60° C. overnight. 5 mL of dimethylformamide was added. The hot mixture was filtered through celite and washed with dichloromethane/methanol. The filtrate was concentrated under reduced pressure to give 30 mg of 5-[3-methoxy-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde which was used in the next step without further purification.

Workup

temperatureThe reaction mixture was heated to 60° C. overnight
filtrationThe hot mixture was filtered through celite
washwashed with dichloromethane/methanol
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-6b96a054a437468db82afb29e91752bb
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851493B2

Reaction notes

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