HCID 67252242, compound → HCID 58292842, compound

HRID 1798275Notes

Reaction equation

HRID 1798275 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[N:19]=[N:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[N:19]=[N:20][C:21]([CH2:24][NH2:25])=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 67252242HCID 67252242, compound

Product 1

HCID 58292842HCID 58292842, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [6-(6-cyano-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.3 g, 0.85 mmol) and 10% Pd/C (0.35 g) in EtOH (20 mL) was hydrogenated at 40 psi for 1 hour. The mixture was filtered through a pad of celite and concentrated in vacuo to give [6-(6-aminomethyl-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.28 g) which was used without further purification. 1H NMR (400 MHz, DMSO): δ 9.29 (s, 1H), 7.88 (d, J=8.8 Hz, 1H), 7.51 (d, J=9.6 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.12 (d, J=1.2 Hz, 1H), 5.55 (dd, J=2.0, 9.2 Hz, 1H), 4.17 (s, 2H), 4.06 (q, J=7.6 Hz, 2H), 3.16 (dd, J=2.4, 15.6 Hz, 1H), 2.35-2.29 (m, 4H), 1.16 (t, J=7.6 Hz, 3H). MS (ESI) m/z=358 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd5e8a8a62774c1a88eb7c90d3503b0e
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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