{(S)-1-[6-Fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester → (S)-1-[6-fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethylamine

HRID 243379Notes

Reaction equation

HRID 243379 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[C:13]2[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:27][C:24]1[CH:25]=[CH:26][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[C:13]=2[CH:23]=1

Participants

4

Reactant 1

HCID 68157759{(S)-1-[6-Fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 68157883(S)-1-[6-fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethylamineYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of {(S)-1-[6-fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (52 mg, 0.14 mmol) in DCM (3 mL) and TFA (1 mL) was stirred at RT for 2 h. The crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge and washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford (S)-1-[6-fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethylamine as a pink oil (37 mg, 96%). LCMS (Method C): RT 1.98 min [M+H]+ 287.2.

Workup

  1. customThe crude reaction mixture
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f02a0b7353ec4cd1b5b0d02649116187
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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