Hydrochloric Acid → 2-((S)-1-Aminoethyl)-5-fluoro-3-pyridin-2-yl-3H-benzoimidazole-4-carbonitrile dihydrochloride

HRID 243065Notes

Reaction equation

HRID 243065 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][N:16]=2)[C:13]2[C:21]([C:26]#[N:27])=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[ClH:29].[NH2:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:13]2[C:21]([C:26]#[N:27])=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68157921[(S)-1-(7-Cyano-6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 681570552-((S)-1-Aminoethyl)-5-fluoro-3-pyridin-2-yl-3H-benzoimidazole-4-carbonitrile dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[(S)-1-(7-Cyano-6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (563 mg, 1.47 mmol) was dissolved in hydrochloric acid in dioxane (10 mL, 4M) and the reaction stirred at RT for 1 h. The reaction mixture was concentrated in vacuo to yield the title compound as an off-white solid (523 mg, 100%). LCMS (Method C): RT=1.75 min, [M+H]+=282.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-17d153e258d242de8f6ef249a6f98c6d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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