Hydrochloric Acid → HCID 59577737, compound

HRID 1947539Notes

Reaction equation

HRID 1947539 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[C:17]3[CH:18]=[CH:19][C:20]([O:22][C:23]4[S:24][C:25]5[C:26]([N:31]=4)=[N:27][CH:28]=[CH:29][CH:30]=5)=[CH:21][C:16]=3[O:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[K+].Cl>CC(O)C>[S:24]1[C:25]2[C:26](=[N:27][CH:28]=[CH:29][CH:30]=2)[N:31]=[C:23]1[O:22][C:20]1[CH:19]=[CH:18][C:17]2[C:13]([CH2:12][N:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)=[CH:14][O:15][C:16]=2[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59577409HCID 59577409, compound

Product 1

HCID 59577737HCID 59577737, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution 1-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-piperidine-4-carboxylic acid ethyl ester (77 mg, 0.18 mmol) in IPA (1.7 mL) was added 2 M KOH (0.9 mL, 1.8 mmol) and stirred (rt, 2 h). The pH of the reaction mixture was adjusted to pH 8 with 1 M HCl (1.7 mL) and partitioned with DCM (30 mL). The aqueous phase was extracted with DCM (3×30 mL). The organic layers were combined, dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (28 mg, 39%). MS (ESI): mass calcd. for C21H19N3O4S, 409.1; m/z found, 410.0 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.49 (dd, J=4.8, 1.4, 1H), 8.31 (dd, J=8.0, 1.5, 1H), 7.98 (5, 1H), 7.89 (d, J=8.6, 1H), 7.75-7.70 (m, 1H), 7.44-7.29 (m, 2H), 4.06 (5, 2H), 3.28-3.08 (m, 2H), 2.72-2.47 (m, 2H), 2.34-2.22 (m, 1H), 2.09-1.95 (m, 2H), 1.93-1.72 (m, 2H). The remaining proton was not detected (COOH).

Workup

  1. custompartitioned with DCM (30 mL)
  2. extractionThe aqueous phase was extracted with DCM (3×30 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53b5469463c54d1ab300653c5519b161
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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