[1-(6-Fluoro-1-pyridin-4-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester → HCID 68157604, compound

HRID 243101Notes

Reaction equation

HRID 243101 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:13]2[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:25][C:22]1[CH:23]=[CH:24][C:12]2[N:11]=[C:10]([CH:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:13]=2[CH:21]=1

Participants

4

Reactant 1

HCID 68157623[1-(6-Fluoro-1-pyridin-4-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157604HCID 68157604, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of [1-(6-fluoro-1-pyridin-4-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (210 mg, 0.59 mmol) in DCM (2 mL) and TFA (1 mL) was stirred at RT for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford the title compound (120 mg, 79%) as a yellow solid. LCMS (Method C): RT 1.63 min [M+H]+ 257.15.

Workup

  1. washwas washed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-803544c996514df19e2159857fd453c8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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