Hydrochloric Acid → HCID 66787649, compound

HRID 1947538Notes

Reaction equation

HRID 1947538 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[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=5[N:27]=4)=[CH:21][C:16]=3[O:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[K+].Cl>CC(O)C>[CH:4]([OH:5])=[O:3].[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[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 59577487HCID 59577487, compound

Product 1

HCID 66787649HCID 66787649, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution 1-[6-(benzothiazol-2-yloxy)-benzofuran-3-ylmethyl]-piperidine-4-carboxylic acid ethyl ester (342 mg, 0.783 mmol) in IPA (8 mL) was added 2 M KOH (3.9 mL, 7.8 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. The resulting residue was purified by reverse phase HPLC to provide the title compound as a colorless solid (86 mg, 24%). MS (ESI): mass calcd. for C22H20N2O4S, 408.1; m/z found, 408.9 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.78-7.64 (m, 4H), 7.56 (d, J=2.0, 1H), 7.41-7.35 (m, 1H), 7.31-7.27 (m, 1H), 3.90 (5, 2H), 3.61 (5, J=135.2, 1H), 3.17 (d, J=11.3, 3H), 2.36 (t, J=10.9, 3H), 2.11-1.77 (m, 4H).

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
  6. customThe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-df6e5fdb61464721bd1bf269872edbc8
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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