Hydrochloric Acid → HCID 59577602, compound

HRID 1947515Notes

Reaction equation

HRID 1947515 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][C:18]([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:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[K+].Cl>C(O)(C)C.O>[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:18]1[CH:17]=[C:16]2[C:21]([C:13]([CH2:12][N:9]3[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)=[CH:14][NH:15]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 49833721HCID 49833721, compound

Product 1

HCID 59577602HCID 59577602, compoundYield 334.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[6-(benzothiazol-2-yloxy)-1H-indol-3-ylmethyl]-piperidine-4-carboxylic acid ethyl ester (410 mg, 0.094 mmol) in isopropanol (10 mL) was added aqueous KOH (2 M, 53 mg, 0.42 mL, 0.94 mmol) and the resulting solution was heated (90° C., 24 h). The reaction mixture was diluted with H2O (10 mL) and neutralized with aqueous 1 M HCl. The suspension was filtered and the solid was washed with EtOAc (20 mL) and dried in vacuo to provide the title compound as a tan solid (128 mg, 33%). MS (ESI): mass calcd. for C22H21N3O3S, 407.4; m/z found, 408.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 11.18 (5, 1H), 7.88 (d, J=9.7, 1H), 7.73 (d, J=10.8, 1H), 7.68 (d, J=10.0, 1H), 7.44-7.40 (m, 2H), 7.35-7.28 (m, 2H), 7.06-7.03 (m, 1H), 3.66 (5, 2H), 2.88-2.84 (m, 2H), 2.22-2.16 (m, 1H), 2.04-2.00 (m, 2H), 1.80-1.77 (m, 2H), 1.58-1.55 (m, 2H), the CO2H proton was not detected.

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with EtOAc (20 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-58b95d24c96549acabf46d77dbb23a3f
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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