HCID 67252450, compound → HCID 58292722, compound

HRID 1798221Notes

Reaction equation

HRID 1798221 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[CH:23]=[N:22][CH:21]=[C:20]([C:24]#[N:25])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]>Cl.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[CH:23]=[N:22][CH:21]=[C:20]([CH2:24][NH2:25])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 1

HCID 67252450HCID 67252450, compound

Product 1

HCID 58292722HCID 58292722, compoundYield 11.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [6-(6-cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (1.35 g, 3.82 mmol), 10% Pd/C (1.35 g) and 6M HCl (2 drops) in EtOH (60 mL) was hydrogenated at 40 psi for 1 hour. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-aminomethyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.16 g, 11.7%). 1H NMR (400 MHz, DMSO-d δ 8.42 (s, 1H), 8.32 (s, 1H), 8.25 (s, 1H), 7.30 (s, 1H), 7.17 (s, 1H), 7.00 (m, 1H), 5.58 (m, 1H), 3.80 (s, 2H), 3.18 (m, 1H), 2.38 (m, 4H), 1.17 (m, 3H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1941acf6aa1c4db1afc85562707313e7
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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