HCID 68157432, compound → HCID 68157847, compound

HRID 243177Notes

Reaction equation

HRID 243177 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH3:15])[C:13]2[C:16]([Br:20])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:20][C:16]1[C:13]2[N:14]([CH3:15])[C:10]([C@@H:8]([NH2:7])[CH3:9])=[N:11][C:12]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 68157432HCID 68157432, compound

Product 1

HCID 68157847HCID 68157847, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [(S)-1-(7-bromo-1-methyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (1.8 g, 5.1 mmol) in TFA (7.5 mL) and DCM (22.5 mL) was stirred for 45 min at RT. The reaction solution was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH, followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford the title compound as a pale red solid (1.3 g, 99%). Marfey's test: 98% de. LCMS (Method C): RT 1.49 min [M+H]+ 415 (for 79Br).

Workup

  1. washThe cartridge was washed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-714adaa233cf40d488e0596c5e29723c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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