Hydrochloric Acid → HCID 67305629, compound

HRID 1260177Notes

Reaction equation

HRID 1260177 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([N:12]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([O:21][CH3:22])[N:14]=2)[CH:9]=[CH:8][C:7]=1[B:30]1OC(C)(C)C(C)(C)[O:31]1)(=O)C.[OH-].[Na+].Cl>CO>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:12]([C:10]2[CH:9]=[CH:8][C:7]3[B:30]([OH:31])[O:4][CH2:5][C:6]=3[CH:11]=2)[C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[N:14][C:15]=1[O:21][CH3:22])#[N:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67307560HCID 67307560, compound

Product 1

HCID 67305629HCID 67305629, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(tert-butoxycarbonyl(5-cyano-6-methoxypyridin-2-yl)amino)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (2.20 g, 3.82 mmol) in methanol (38 mL) was added 1 mol/L sodium hydroxide (11.5 mL, 11.5 mmol). The reaction was stirred at room temperature for three hours and was then neutralized with 1 mol/L hydrochloric acid until pH=6 to 7. The solvent was removed under reduced pressure and the mixture was extracted with ethyl acetate and the organic layer was washed with an aqueous boric acid solution (0.5 M) five times. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column using Combiflash to give tert-butyl 5-cyano-6-methoxypyridin-2-yl(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)carbamate (1.302 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36 (s, 9H), 3.50 (s, 2H), 4.94 (s, 2H), 7.14 (dd, J=1.8, 7.8 Hz, 1H), 7.22 (s, 1H), 7.38 (d, J=8.4 Hz, 1H), 7.71 (d, J=7.8 Hz, 1H), 8.17 (d, J=8.4 Hz, 1H), 9.19 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with an aqueous boric acid solution (0.5 M) five times
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by column

Sources & evidence

ORD record
ord-2cc221daac534d6d884455a9fc77ab8a
Source dataset
uspto-grants-2013_06
Patent number
US08470803B2

Reaction notes

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