HCID 67253812, compound → HCID 58292552, compound

HRID 1798230Notes

Reaction equation

HRID 1798230 reaction equation
C([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][C:21]([C:24]#[N:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C>CO.[Pd]>[NH2:25][CH2:24][C:21]1[N:22]=[CH:23][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:26])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:19][CH:20]=1

Participants

4

Reactant 1

HCID 67253812HCID 67253812, compound

Product 1

HCID 58292552HCID 58292552, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of [6-(5-cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (1.63 g) and Pd/C (250 mg) in methanol (80 mL) was degassed 3 times and the suspension was charged with H2 balloon at room temperature overnight. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated to dryness, affording the title compound (1.45 g). 1H NMR (300 MHz, CD3OD) δ 8.49 (s, 1H), 8.44 (s, 1H), 8.21 (s, 1H), 7.21 (s, 1H), 7.10 (s, 1H), 5.70-5.66 (m, 1H), 4.29 (s, 2H), 4.19 (q, 2H), 3.22-3.16 (m, 1H), 2.54-2.46 (m, 1H), 2.40 (s, 3H), 1.24 (t, 3H). MS found: (M+H)+=358.2.

Workup

  1. customwas degassed 3 times
  2. additionthe suspension was charged with H2 balloon at room temperature overnight
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-951c1760753e4abbbe0caee57d50153a
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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