Hydrochloric Acid → HCID 67439383, compound

HRID 1471569Notes

Reaction equation

HRID 1471569 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:19]=[C:18]([O:20][CH2:21][CH2:22][O:23]C4CCCCO4)[C:15]([C:16]#[N:17])=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1.Cl.CCOCC>CO>[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:19]=[C:18]([O:20][CH2:21][CH2:22][OH:23])[C:15]([C:16]#[N:17])=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67440685HCID 67440685, compound

Product 1

HCID 67439383HCID 67439383, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 6-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-nicotinonitrile (1.8 g, 4.54 mmol) in methanol (15 mL) at 0° C. was added 1M HCl in ether (5.45 ml, 5.45 mmol) and left at the same temperature for 2 h. The solid that formed was collected by filtration and dissolved in minimum volume of 10% MeOH/CHCl3 and passed through a short column. The solvent was evaporated to yield the title compound (D119) (0.28 g, 20%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (s, 1 H), 8.45 (s, 1 H), 7.77 (d, J=7.8 Hz, 1 H), 7.22 (s, 1 H), 7.15-7.09 (m, 1 H), 7.01 (s, 1 H), 5.04 (t, J=5.3 Hz, 1 H), 4.99 (s, 2 H), 4.30 (t, J=4.5 Hz, 2 H), 3.79-3.76 (m, 2 H); MS (ES) m/z: 313 (M+1)+; HPLC purity 99.27% (Maxplot), 99.66% (220 nm). Elemental analysis for C15H13BN2O5: Calculated C: 57.73; H: 4.20; N: 8.98. found C: 57.53; H: 4.31; N: 8.95.

Workup

  1. customThe solid that formed
  2. filtrationwas collected by filtration
  3. dissolutiondissolved in minimum volume of 10% MeOH/CHCl3
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a8119aa92bc24a598234c7e01e8a2594
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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