[(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester → (S)-2-(1-Aminoethyl)-1-phenyl-1H-benzo[D]imidazole-6-carbonitrile

HRID 242804Notes

Reaction equation

HRID 242804 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[CH:21]=[C:22]([C:25]#[N:26])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:7][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[CH:21]=[C:22]([C:25]#[N:26])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9]

Participants

3

Reactant 1

HCID 68157544[(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

Product 1

HCID 68157742(S)-2-(1-Aminoethyl)-1-phenyl-1H-benzo[D]imidazole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (1.97 mmol) in TFA (3 mL) was stirred at RT for 30 min. Volatiles were removed under reduced pressure and the resulting residue was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3/MeOH. The product was further purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording 2-((S)-1-Aminoethyl)-3-phenyl-3H-benzoimidazole-5-carbonitrile as white crystalline solid (415 mg, 80% over two steps). LCMS: RT 1.99 min [M+H]+ 263.2

Workup

  1. customVolatiles were removed under reduced pressure
  2. washThe cartridge was washed with MeOH
  3. washthe product eluted with 2M NH3/MeOH
  4. customThe product was further purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-d30f876c32f44c73b9fdcb89c3535097
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…