Lithium Hydroxide → HCID 66787093, compound

HRID 1947504Notes

Reaction equation

HRID 1947504 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][C:16]3[S:17][C:18]4[C:19]([N:24]=3)=[N:20][CH:21]=[CH:22][CH:23]=4)=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])C.[Li+].[OH-]>C1COCC1>[CH:4]([OH:5])=[O:3].[S:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:24]=[C:16]1[O:15][C:13]1[CH:12]=[CH:11][C:10]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][O:8][C:9]=2[CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 66787145HCID 66787145, compound

Product 1

HCID 66787093HCID 66787093, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-carboxylic acid ethyl ester (200 mg, 0.59 mmol) in THF (6 mL) was added 4 N LiOH (0.15 mL, 0.59 mmol). Two additional aliquots of 4 N LiOH (each 0.30 mL) were added over 2 h. The mixture was stirred (rt, 24 h). The reaction mixture was partially concentrated in vacuo. The remaining aqueous solution was purified by reverse phase HPLC to provide the title compound as a white solid (92 mg, 44%). MS (ESI): mass calcd. for C15H8N2O4S, 312.02; m/z found, 312.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.78 (s, 1H), 8.53 (dd, J=4.8, 1.7, 1H), 8.43 (dd, J=8.0, 1.7, 1H), 8.09 (d, J=8.6, 1H), 8.04 (d, J=2.1, 1H), 7.56-7.50 (m, 1H), 7.41-7.32 (m, 1H). The remaining proton was not detected and is believed to be hidden in the solvent peak.

Workup

  1. concentrationThe reaction mixture was partially concentrated in vacuo
  2. customThe remaining aqueous solution was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-47bb197b820e492db543554b47130ddb
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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