Water → HCID 57448290, compound

HRID 1807467Notes

Reaction equation

HRID 1807467 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:28]=[CH:27][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24]CC)=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1.[OH-].[K+].O>C(O)(C)C>[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:12]=[CH:13][C:14]([CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 44480811HCID 44480811, compound

Product 1

HCID 57448290HCID 57448290, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 1-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)benzyl]piperidine-4-carboxylate (97 mg, 0.24 mmol) in isopropyl alcohol (750 μL) was added 1 N KOH (240 μL). The mixture was allowed to stir at rt for 2 h. The reaction mixture was then poured into water (20 mL) and basified to pH 9. The resultant solution was extracted with a 1:1 solution of CHCl3/isopropyl alcohol (2×30 mL). The combined organic extracts were dried, filtered, and concentrated to afford the title compound (38 mg, 43%). 1H NMR (400 MHz, CD3OD): 8.49 (d, J=4.8, 1H), 8.32 (dd, J=8.0, 1.6, 1H), 7.61-7.54 (m, 2H), 7.52-7.45 (m, 2H), 7.35 (dd, J=8.0, 4.9, 1H), 3.95 (s, 2H), 3.22-3.09 (m, 2H), 2.65-2.46 (m, 1H), 2.38-2.22 (m, 1H), 2.05-1.92 (m, 2H), 1.91-1.75 (m, 2H), 0.98-0.79 (m, 1H). MS (ESI): mass calcd for C19H19N3O3S, 369.12; m/z found, 370.2 [M+H]+.

Workup

  1. extractionThe resultant solution was extracted with a 1:1 solution of CHCl3/isopropyl alcohol (2×30 mL)
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-84683850b1e64e59a814538f37005370
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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