3,3-Dimethylbutanoyl chloride → HCID 178429851, compound

HRID 2245383Notes

Reaction equation

[CH2:1]=[C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH2:3]1.CCN(C(C)C)C(C)C.[CH3:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34](Cl)=[O:35]>C(#N)C.C(Cl)Cl>[CH3:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34](/[N:7]=[C:5]1\[S:6][C:2](=[CH2:1])[CH2:3][N:4]\1[C:8]1[CH:21]=[CH:20][C:11]2[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=2[CH:9]=1)=[O:35]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5-methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine (Example 22C, 0.14 g, 0.44 mmol) in acetonitrile (3 mL) was added Hunig's base (0.062 g, 0.48 mmol) followed by 3,3-dimethylbutanoyl chloride (0.088 g, 0.66 mmol). The mixture was heated for 12 hours at 65° C. The reaction mixture was cooled down, diluted with CH2Cl2 (50 mL), and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and dried. After evaporation under reduced pressure, the residue was chromatographed over silica using CH2Cl2-5%MeOH/CH2Cl2 to supply the titled compound. 1H NMR (CDCl3) δ ppm 1.00 (9H), 2.35 (2H), 4.65 (2H), 5.25 (1H), 5.35 (1H), 7.15 (1H), 7.25 (1H), 7.55 (1H); MS (ESI) m/z 419 (M+H)+.

Workup

temperatureThe reaction mixture was cooled down
washwashed with water and brine
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
customdried
customAfter evaporation under reduced pressure
customthe residue was chromatographed over silica

Sources & evidence

ORD record: ord-e84f01c3145b41cfb2d4c7a1235316c3
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683084B2

Reaction notes

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