Hydrochloric Acid → HCID 58292565, compound

HRID 1798225Notes

Reaction equation

HRID 1798225 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[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)C.[Li+].[OH-].Cl>C1COCC1.O>[NH2:25][CH2:24][C:23]1[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]=[CH:21][N:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292618HCID 58292618, compound

Product 1

HCID 58292565HCID 58292565, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-(3-aminomethyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (190 mg, 0.532 mmol) in THF (5 mL) and H2O (2 mL) was added LiOH (0.111 g, 2.66 mmol). The resulting solution was stirred at room temperature overnight. The mixture was diluted with H2O and acidified to pH 3 with 1N HCl. The resulting mixture was concentrated and the residue was purified by prep HPLC. The title compound was obtained (100 mg, 57%) as a white solid. 1H NMR (CD3OD) δ8.30 (d, 1H), 8.07 (d, 1H), 7.21 (d, 1H), 7.09 (d, 1H), 5.66 (dd, 1H), 4.47 (s, 2H), 3.14 (dd, 1H), 2.37 (s, 3H), 2.30 (dd, 1H). MS calcd for (C15H16BN3O5+H)+: 330. MS found: (M+H)+=330.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-c2260d55a3e64c76b097f92a22fe4267
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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