Trifluoroacetic acid → (S)-1-(7-Bromo-1-cyclopropyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamine

HRID 243141Notes

Reaction equation

HRID 243141 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:17]1[N:21]([CH:22]2[CH2:24][CH2:23]2)[C:20]2[C:25]([Br:30])=[C:26]([F:29])[CH:27]=[CH:28][C:19]=2[N:18]=1)[CH3:16])(C)(C)C>C(Cl)Cl.CO>[Br:30][C:25]1[C:20]2[N:21]([CH:22]3[CH2:23][CH2:24]3)[C:17]([C@@H:15]([NH2:14])[CH3:16])=[N:18][C:19]=2[CH:28]=[CH:27][C:26]=1[F:29]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157376[(S)-1-(7-Bromo-1-cyclopropyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157092(S)-1-(7-Bromo-1-cyclopropyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamineYield 88.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of [(S)-1-(7-bromo-1-cyclopropyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (133 mg, 0.33 mmol) in DCM (3 mL). After stirring at RT for 2 h, the reaction mixture was diluted with MeOH and 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 colourless oil (87 mg, 87%). LCMS (Method C): RT 1.99 min [M+H]+ 298.10

Workup

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

Sources & evidence

ORD record
ord-77e1f71243824d00892a568cfd93ab5d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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