Acetonitrile → HCID 135416291, compound

HRID 1361478Notes

Reaction equation

Br[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:8]2)[S:4][N:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[OH:35])O1.C([O-])([O-])=O.[K+].[K+].CC#N>O>[OH:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:8]2)[S:4][N:3]=1

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of isobutyl 1-(3-bromo-1,2,4-thiadiazol-5-yl)piperidin-4-ylcarbamate (0.38 g, 1.1 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (0.35 g, 1.6 mmol), Pd(Ph3)4 (12 mg, 11 μmol), K2CO3 (0.29 g, 2.1 mmol), CH3CN (3.0 mL), and H2O (0.3 mL) was sealed in a microwave vessel and heated by microwave irradiation at 175° C. for 15 minutes. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to yield isobutyl 1-(3-(2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)piperidin-4-ylcarbamate. LC/MS: m/z 377.3 (M+H)+ at 3.77 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

customwas sealed in a microwave vessel
temperatureThe reaction was cooled to room temperature
extractionextracted with CH2Cl2
washThe combined extracts were washed with water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record: ord-0aee4fdbcb064da899874064683c96fb
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880008B2

Reaction notes

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