Hydrochloric Acid → HCID 67251860, compound

HRID 1798232Notes

Reaction equation

HRID 1798232 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].Cl[C:20]1[CH:25]=[N:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][N:21]=1.[H-].[Na+].Cl>CN(C=O)C>[CH3:29][O:28][C:26]([C:23]1[CH:22]=[N:21][C:20]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[CH:25][N:24]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 67251860HCID 67251860, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (2 g, 8 mmol) and methyl 2-chloro-5-pyrazinecarboxylate (1.95 g, 12 mmol) in DMF (40 mL) at 0° C. was added NaH (0.8 g, 20 mmol). The reaction mixture was allowed to warm up to room temperature slowly and heated at 50° C. for 1 h. The reaction mixture was cooled down and acidified to pH 3 with 6N HCl, extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, DCM/MeOH=9:1) affording the title compound (1.9 g, 61%) as a light yellow solid. 1H NMR (CDCl3) δ 8.82 (s, 1H), 8.53 (s, 1H), 7.38 (d, 1H), 7.07 (d, 1H), 5.69 (dd, 1H), 4.10 (q, 2H), 4.02 (s, 3H), 3.06 (dd, 1H), 2.43 (m, 1H), 2.39 (s, 3H), 1.23 (t, 3H).

Workup

  1. temperatureheated at 50° C. for 1 h
  2. temperatureThe reaction mixture was cooled down
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica, DCM/MeOH=9:1)

Sources & evidence

ORD record
ord-dba38008c7844be995431b4b1b1281f3
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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