HCID 58292872, compound → HCID 58292618, compound

HRID 1798224Notes

Reaction equation

HRID 1798224 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[C:23]([C:24]#[N:25])=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]>CO.Cl.[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[C:23]([CH2:24][NH2:25])=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 1

HCID 58292872HCID 58292872, compound

Product 1

HCID 58292618HCID 58292618, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [6-(3-cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (200 mg, 0.566 mmol) in MeOH (10 mL) was added Pd/C (20 mg), HCl (conc., 2 drops). The resulting solution was degassed, and reacted under 1-atm H2 balloon for 6 hrs. The mixture was filtrated. The filtration was removed in vacuo to afford the title compound (190 mg, 94%) as a light yellow solid. MS found: (M+H)+=358.

Workup

  1. customThe resulting solution was degassed
  2. customreacted under 1-atm H2 balloon for 6 hrs
  3. filtrationThe mixture was filtrated
  4. filtrationThe filtration
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-b8b1066426024c10a23d00faf4a00d40
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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