Triethylamine → HCID 178470805, compound

HRID 1798235Notes

Reaction equation

HRID 1798235 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][C:21]([C:24]#[N:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].Cl.[NH2:28][OH:29].C(N(CC)CC)C>CO>[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][C:21]([C:24](=[NH:25])[NH:28][OH:29])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67253812HCID 67253812, compound

Product 1

HCID 178470805HCID 178470805, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[6-(5-Cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (200 mg, 0.57 mmol) and hydroxylamine hydrochloride (99 mg, 1.4 mmol) were mixed in methanol (5.4 mL). To this was added triethylamine (0.28 mL, 2 mmol). The reaction was stirred at room temperature overnight. The solvent was removed. The residue was dissolved in dichloromethane and washed with water. The organic layer was separated and the solvent was removed to give a residue. The residue was dried under high vacuum to give the title compound (174 mg, 79%) as a white solid. MS found (electrospray): (M+H)+=387.1.

Workup

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe organic layer was separated
  5. customthe solvent was removed
  6. customto give a residue
  7. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-62928df82993469d9c2edb7d314fd8c5
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…