Trifluoroacetic acid → (S)-1-[6-Fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propylamine

HRID 243179Notes

Reaction equation

HRID 243179 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:18]1[N:22]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([F:29])[CH:28]=2)[C:21]2[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:20]=2[N:19]=1)[CH2:16][CH3:17])(C)(C)C>C(Cl)Cl>[F:34][C:31]1[CH:32]=[CH:33][C:20]2[N:19]=[C:18]([C@@H:15]([NH2:14])[CH2:16][CH3:17])[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([F:29])[CH:28]=3)[C:21]=2[CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157999{(S)-1-[6-Fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propyl}carbamic acid tert-butyl ester

Product 1

HCID 68157014(S)-1-[6-Fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propylamineYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.12 mL, 1.58 mmol) was added to a solution of {(S)-1-[6-fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propyl}carbamic acid tert-butyl ester (123 mg, 0.33 mmol) in DCM (2 mL) and the reaction stirred at RT for 18 h. The reaction mixture was concentrated in vacuo and passed through a 2 g Isolute® SCX-2 cartridge, eluting with 2M NH3/MeOH. The basic fraction was concentrated in vacuo to give the title compound (92 mg, quant.) as brown oil. LCMS (Method J): RT=1.86 min, [M+H]+=289.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washeluting with 2M NH3/MeOH
  3. concentrationThe basic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-ab462502d29a47bab613f1cea5f0c049
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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