Hydrochloric Acid → (S)-1-(6-Fluoro-7-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

HRID 243240Notes

Reaction equation

HRID 243240 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[C:21]([O:26][CH3:27])=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.[ClH:29]>CO.O1CCOCC1>[ClH:29].[ClH:29].[F:25][C:22]1[CH:23]=[CH:24][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13]=2[C:21]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68157871[(S)-1-(6-Fluoro-7-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68157332(S)-1-(6-Fluoro-7-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

[(S)-1-(6-Fluoro-7-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (349 mg, 0.91 mmol) was dissolved in methanol (1 mL) and hydrochloric acid in dioxane (3 mL, 4M) and the reaction stirred at RT for 1 hour. The reaction mixture was concentrated in vacuo to yield the title compound as an off-white solid (321 mg, 100%). LCMS (Method C): RT=2.02 min, [M+H]+=286.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-eb2d4840621f4bddac1c483eabfe7651
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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