Hydrochloric Acid → HCID 67439951, compound

HRID 1471610Notes

Reaction equation

HRID 1471610 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1.CCO.C1COCC1.[ClH:28]>CO.CCOCC>[ClH:28].[NH2:17][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[B:2]([OH:1])[O:3][CH2:4][C:5]=3[CH:10]=2)=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8028TetrahydrofuranHCID 24966976HCID 24966976, compound

Product 1

HCID 67439951HCID 67439951, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a 50 mL round-bottom flask fitted with magnetic stirring bar was added 6-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-nicotinonitrile (1.0 g, 4.0 mmol, 1.0 eq.), followed by addition of EtOH (40 mL) and THF (15 mL). The flask was evacuated and recharged with N2 twice. To the stirring solution was added 5% Pd/C (300 mg) and the flask was evacuated and recharged with H2 three times. The resulting suspension was stirred under a H2 balloon at room temperature over 3 days. The mixture was filtered through a short pack of celite and washed with EtOH (3×25 mL). The combined filtrate was concentrated under reduced pressure, the residue was applied to silica chromatography eluting with MeOH/DCM (0:100 to 10:90) to give a white solid. The solid was dissolved in minimum amount of MeOH and carefully treated with HCl in Et2O. The precipitate was collected by filtration and washed with Et2O to give 5-(5-aminomethyl-pyridin-2-yloxy)-3H-benzo[c][1,2]oxaborol-1-ol hydrochloride a white solid. 1H NMR (DMSO-d6) δ: 9.95 (br. s., 1H), 8.28 (d, J=2.2 Hz, 1H), 8.11 (dd, J=8.5, 2.4 Hz, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.07-7.14 (m, 2H), 7.05 (dd, J=7.9, 2.0 Hz, 1H), 4.94 (s, 2H), 4.14 (t, J=5.6 Hz, 2H).

Workup

  1. customTo a 50 mL round-bottom flask fitted with magnetic stirring bar
  2. customThe flask was evacuated
  3. additionTo the stirring solution was added 5% Pd/C (300 mg)
  4. customthe flask was evacuated
  5. filtrationThe mixture was filtered through a short pack of celite
  6. washwashed with EtOH (3×25 mL)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. washeluting with MeOH/DCM (0:100 to 10:90)
  9. customto give a white solid
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with Et2O

Sources & evidence

ORD record
ord-1824eab9f87a44db8bf3aec9361a26ca
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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