Water → HCID 46174397, compound

HRID 1260178Notes

Reaction equation

HRID 1260178 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:11]([C:19]2[CH:28]=[CH:27][C:22]3[B:23]([OH:26])[O:24][CH2:25][C:21]=3[CH:20]=2)C(=O)OC(C)(C)C)=[N:7][C:8]=1[O:9][CH3:10])#[N:2].[OH-].[Na+].O>Cl.O1CCOCC1>[OH:26][B:23]1[C:22]2[CH:27]=[CH:28][C:19]([NH:11][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[C:8]([O:9][CH3:10])[N:7]=3)=[CH:20][C:21]=2[CH2:25][O:24]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67305629HCID 67305629, compound

Product 1

HCID 46174397HCID 46174397, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 5-cyano-6-methoxypyridin-2-yl(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)carbamate (0.944 g, 2.48 mmol) in 4 mol/L hydrogen chloride in dioxane (20 mL) was stirred at room temperature for three hours. The solution was then neutralized with 6 mol/L sodium hydroxide until pH=6 to 7. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The aqueous layer contained precipitate, which was collected by filtration and dried under reduced pressure. The residue was purified by Combiflash to give 6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-ylamino)-2-methoxynicotinonitrile (0.086 g, 9.1%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.95 (s, 2H), 6.50 (d, J=8.4 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 9.00 (s, 1H), 9.94 (s, 1H).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure
  8. customThe residue was purified by Combiflash

Sources & evidence

ORD record
ord-7e4deadc79c346dcb7efba299850ce0d
Source dataset
uspto-grants-2013_06
Patent number
US08470803B2

Reaction notes

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