Hydrochloric Acid → HCID 58292872, compound

HRID 1798223Notes

Reaction equation

[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.Cl[C:20]1[C:21]([C:26]#[N:27])=[N:22][CH:23]=[CH:24][N:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH:4]1[O:3][B:2]([OH:1])[C:6]2[CH:7]=[C:8]([O:12][C:20]3[C:21]([C:26]#[N:27])=[N:22][CH:23]=[CH:24][N:25]=3)[CH:9]=[C:10]([CH3:11])[C:5]1=2)[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.0 g, 4.0 mmol) and 3-chloro-pyrazine-2-carbonitrile (0.84 g, 6.0 mmol) in DMF (24 mL) was added cesium carbonate (2.68 g, 8.8 mmol). The mixture was heated to 80° C. for 2 hrs. The reaction was cooled down, diluted with H2O, acidified to pH 3 with aqueous HCl (1N). The mixture was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by column chromatography (silica, Hexanes/Ethyl acetate=1:4) affording the title compound (1.30 g, 92%) as a white solid. 1H NMR (CDCl3) δ 8.40 (d, 1H), 8.29 (d, 1H), 7.36 (d, 1H), 7.11 (d, 1H), 5.69 (dd, 1H), 4.81 (s, 1H), 4.20 (q, 2H), 3.11 (dd, 1H), 2.44 (dd, 1H), 2.39 (s, 3H), 1.26 (t, 3H). MS found: (M+H)+=354.

Workup

temperatureThe reaction was cooled down
extractionThe mixture was extracted with ethyl acetate
customThe organic phase was separated
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified by column chromatography (silica, Hexanes/Ethyl acetate=1:4)

Sources & evidence

ORD record: ord-80d224412dff4e89a0920fed520ba98c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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