Hydrochloric Acid → HCID 66774305, compound

HRID 1644289Notes

Reaction equation

HRID 1644289 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[CH:19]=[C:18]2[C:28]([O:30][CH3:31])=[O:29])[CH2:11][CH2:10]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[CH:19]=[C:18]2[C:28]([O:30][CH3:31])=[O:29])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66774230HCID 66774230, compound2×

Product 1

HCID 66774305HCID 66774305, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of methyl 1-(2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl)-6-methoxy-1H-indole-2-carboxylate (Intermediate 13, 520 mg, 1.2 mmol) in dioxane (4 mL) was treated at room temperature under vigorous stirring with a solution of HCl in dioxane (4M, 2 mL). After 3 days, the reaction mixture was concentrated under reduced pressure. The residue was taken up in dichloromethane (60 mL) and saturated aqueous sodium hydrogen carbonate solution (10 mL), the aqueous phase was extracted three times with dichloromethane (3×50 mL) and the combined organic phases were dried over sodium sulfate to give 407 mg (100% yield) of the crude product as colorless solid, mp 101° C.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionsaturated aqueous sodium hydrogen carbonate solution (10 mL), the aqueous phase was extracted three times with dichloromethane (3×50 mL)
  3. dry with materialthe combined organic phases were dried over sodium sulfate

Sources & evidence

ORD record
ord-618a7ef48ebb4ac081e44fa3f42f62fa
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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