Trifluoroacetic acid → HCID 68156985, compound

HRID 243013Notes

Reaction equation

HRID 243013 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:15]2[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:14]=2[N:13]=1)[CH2:9][O:10][CH3:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:27][C:24]1[CH:25]=[CH:26][C:14]2[N:13]=[C:12]([C@@H:8]([NH2:7])[CH2:9][O:10][CH3:11])[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:15]=2[CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68158270HCID 68158270, compound

Product 1

HCID 68156985HCID 68156985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(R)-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)-2-methoxyethyl]carbamic acid tert-butyl ester (419 mg, 1 mmol) in DCM (6 mL) was added TFA (3 mL) and the mixture was stirred at RT for 2 h. The volatiles were removed in vacuo and the resulting residue 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. The crude material was used in the following step without further purification: yellow oil (135 mg, 47%). LCMS (Method B): RT 1.71 min [M+H]+ 287.01.

Workup

  1. customThe volatiles were removed in vacuo
  2. washThe cartridge was washed with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe crude material was used in the following step without further purification
  5. customRT 1.71 min [M+H]+ 287.01

Sources & evidence

ORD record
ord-b36f8857a6844cf6bfe2bfcb5f6ce7b0
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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