Hydrochloric Acid → HCID 59577555, compound

HRID 1947514Notes

Reaction equation

HRID 1947514 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:31][C@H:30]([O:32][Si](C(C)(C)C)(C)C)[CH2:29][C:28]4=[O:40])[CH2:23][CH2:22]3)=[CH:16][NH:17]2)=[CH:13][CH:12]=1.Cl>CO.C(Cl)Cl.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:31][C@H:30]([OH:32])[CH2:29][C:28]4=[O:40])[CH2:23][CH2:22]3)=[CH:16][NH:17]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59577395HCID 59577395, compound

Product 1

HCID 59577555HCID 59577555, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (R)-1-{1-[6-(benzothiazol-2-yloxy)-1H-indol-3-ylmethyl]-piperidin-4-yl}-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one (200 mg, 0.35 mmol) in MeOH:DCM (1:1, 15 mL) was added 4 M HCl in dioxane (5 mL) and the resulting reaction mixture was stirred (rt, 3 h). The reaction mixture was concentrated in vacuo to provide the title compound as a tan solid (112 mg, 70%). MS (ESI): mass calcd. for C25H26N4O3S, 462.5; m/z found, 463.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.00 (br s, 1H), 7.73-7.71 (m, 2H), 7.62 (d, J=7.9, 1H), 7.39-7.33 (m, 2H), 7.28-7.23 (m, 1H), 7.12-7.07 (m, 2H), 4.35 (t, J=8.4, 1H), 3.95-3.90 (m, 1H), 3.69 (s, 2H), 3.37-3.33 (m, 1H), 3.21-3.15 (m, 1H), 3.04-3.02 (m, 2H), 3.41-3.38 (m, 1H), 2.10-2.04 (m, 2H), 1.94-1.89 (m, 1H), 1.77-1.73 (m, 2H), 1.64-1.60 (m, 2H)

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-eec71b60bb06477392d48e59d8e91d65
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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