3,3-Dimethylbutanoyl chloride → HCID 178429851, compound

HRID 1260363Notes

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 (9 H), 2.35 (2 H), 4.65 (2 H), 5.25 (1 H), 5.35 (1 H), 7.15 (1 H), 7.25 (1 H), 7.55 (1 H); 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-d8612ba2949945878f8513182fc6e3cc
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470813B2

Reaction notes

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