Lithium Hydroxide → HCID 66786516, compound

HRID 1947541Notes

Reaction equation

HRID 1947541 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][N:7]([CH3:28])[CH2:8][C:9]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][C:19]3[S:20][C:21]4[C:22]([N:27]=3)=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][C:12]=2[O:11][CH:10]=1)C.[Li+].[OH-]>C1COCC1>[CH:4]([OH:29])=[O:3].[CH3:28][N:7]([CH2:8][C:9]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][C:19]3[S:20][C:21]4[C:22]([N:27]=3)=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][C:12]=2[O:11][CH:10]=1)[CH2:6][CH2:5][C:4]([OH:29])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59577636HCID 59577636, compound

Product 1

HCID 66786516HCID 66786516, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{methyl-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-amino}-propionic acid ethyl ester (30 mg, 0.07 mmol) in THF (0.75 mL) was added 4 N LiOH (0.1 mL). The mixture was stirred (rt, 6.5 h). Purification by reverse phase HPLC provided the title compound as a white solid (7 mg, 21%). MS (ESI): mass calcd. for C19H17N3O4S, 383.09; m/z found, 384.9 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.49 (dd, J=4.9, 1.6, 1H), 8.32 (dd, J=8.0, 1.6, 1H), 8.15 (s, 1H), 7.97-7.92 (m, 1H), 7.80 (d, J=2.1, 1H), 7.44 (dd, J=8.6, 2.1, 1H), 7.38-7.32 (m, 1H), 4.48 (s, 2H), 3.35 (t, J=6.5, 2H), 2.80 (s, 3H), 2.66 (t, J=6.5, 2H).

Workup

  1. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-24e0c2d8ad5740c4bb366ede406564c4
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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