Sodium Hydroxide → N-[4-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzyl]-beta-alanine

HRID 547365Notes

Reaction equation

HRID 547365 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C[O:20][C:21](=[O:25])[CH2:22][CH2:23][NH2:24].[OH-].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:24][CH2:23][CH2:22][C:21]([OH:25])=[O:20])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 192794Methyl beta-alanateHCID 5049666Sodium triacetoxyborohydrideHCID 574483844-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzaldehyde

Product 1

HCID 44479299N-[4-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzyl]-beta-alanineYield 31.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)-benzaldehyde (100 mg, 0.39 mmol) and β-alanine methyl ester (54 mg, 0.39 mmol, 1 equiv.) was added methanol (2 mL) followed by 1 N NaOH (430 μL). The reaction was allowed to stir at rt for 1 h before the addition of sodium triacetoxyborohydride (95 mg, 0.39 mmol, 1 equiv.). Stirring was allowed to continue for 4 h before the reaction was concentrated and purified using preparative reversed phase HPLC to afford the product as white powder (40 mg, 31%). 1H NMR (400 MHz, CD3OD): 8.49 (d, J=4.8, 1H), 8.33 (d, J=7.9, 1H), 8.27 (s, 1H), 7.65 (d, J=8.2, 2H), 7.55 (d, J=8.2, 2H), 7.38-7.33 (m, 1H), 4.28 (s, 2H), 3.24 (t, J=6.4, 2H), 2.58 (t, J=6.4, 2H). MS (ESI): Mass calcd for C16H15N3O3S, 329.08; m/z found, 330.1 [M+H]+.

Workup

  1. concentrationwas concentrated
  2. custompurified

Sources & evidence

ORD record
ord-dc04a1d7b2874410aa485a0ec2ba3234
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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