Hydrochloric Acid → HCID 178419344, compound

HRID 1625499Notes

Reaction equation

HRID 1625499 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([C@@H:19]4[CH2:23][CH2:22][CH2:21][N:20]4C(OC(C)(C)C)=O)[NH:17][CH:18]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[ClH:31]>C(OCC)C>[ClH:31].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([C@@H:19]4[CH2:23][CH2:22][CH2:21][NH:20]4)[NH:17][CH:18]=3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451913HCID 178451913, compound

Product 1

HCID 178419344HCID 178419344, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of (S)-tert-butyl 2-(4-(4′-bromo-[1,1′-biphenyl]-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (505 mg, 1.078 mmol) in HCl (4M in dioxane 5.4 mL, 21.6 mmol) is stirred at room temperature for 2 hours and diluted with diethyl ether (2 mL). The suspension is cooled in an ice bath and the product is collected by filtration to give (S)-4-(4′-bromo-[1,1′-biphenyl]-4-yl)-2-(pyrrolidin-2-yl)-1H-imidazole hydrochloride (436 mg, 99%).

Workup

  1. temperatureThe suspension is cooled in an ice bath
  2. filtrationthe product is collected by filtration

Sources & evidence

ORD record
ord-7d1b5e1432534fda9e202fd4c0016475
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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