Trifluoroacetic acid → [2-((S)-1-Aminoethyl)-3-cyclopropyl-5-fluoro-3H-benzoimidazol-4-yl]-morpholin-4-yl-methanone

HRID 243143Notes

Reaction equation

HRID 243143 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]([C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:31])=[C:26]([F:29])[CH:27]=[CH:28][C:19]=2[N:18]=1)[CH3:16])(C)(C)C>C(Cl)Cl.CO>[NH2:14][C@H:15]([C:17]1[N:21]([CH:22]2[CH2:23][CH2:24]2)[C:20]2[C:25]([C:30]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[O:31])=[C:26]([F:29])[CH:27]=[CH:28][C:19]=2[N:18]=1)[CH3:16]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157617{(S)-1-[1-Cyclopropyl-6-fluoro-7-(morpholine-4-carbonyl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 68158081[2-((S)-1-Aminoethyl)-3-cyclopropyl-5-fluoro-3H-benzoimidazol-4-yl]-morpholin-4-yl-methanoneYield 73.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a stirring solution of {(S)-1-[1-cyclopropyl-6-fluoro-7-(morpholine-4-carbonyl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (380 mg, 0.88 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 pale yellow oil (214 mg, 73%). LCMS (Method B): RT 1.62 and 1.70 min [M+H]+ 333.12

Workup

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

Sources & evidence

ORD record
ord-f90ad8202d544973940e4335a660555c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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