Trifluoroacetic acid → HCID 68157346, compound

HRID 242814Notes

Reaction equation

HRID 242814 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:25][C:23]1[CH:22]=[CH:21][C:13]2[N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:10]([C@@H:8]([NH2:7])[CH3:9])=[N:11][C:12]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157104HCID 68157104, compound

Product 1

HCID 68157346HCID 68157346, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(5-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (912 mg, 2.59 mmol) in DCM (10 mL) was added TFA (5 mL) and the mixture was stirred at RT for 2 h. Volatiles were removed under reduced pressure and the resulting residue was dissolved in DCM (40 mL) and washed with a saturated solution of NaHCO3 (50 mL). The two phase system was stirred for 10 min, then the organic layer was dried (Na2SO4) and concentrated in vacuo affording (S)-1-(5-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine (617 mg, 95%). LCMS: RT 2.10 and 2.23 min [M−NH2] 252.0.

Workup

  1. customVolatiles were removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in DCM (40 mL)
  3. washwashed with a saturated solution of NaHCO3 (50 mL)
  4. stirringThe two phase system was stirred for 10 min
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe1f3282b3d0454eb4e6820c5b1bfd9e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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