Trifluoroacetic acid → 1-(2-Amino-ethyl)-3-methyl-1,3-dihydro-benzoimidazol-2-one

HRID 1749509Notes

Reaction equation

HRID 1749509 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)[C:3]1=[O:21].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:13][CH2:12][CH2:11][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:2]([CH3:1])[C:3]1=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131733591tert-butyl (2-(3-Methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethyl)carbamate

Product 1

HCID 289166861-(2-Amino-ethyl)-3-methyl-1,3-dihydro-benzoimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (100 mg, 0.345 mmol) in DCM (3 mL) was added TFA (1.5 mL) at 0° C. to 5° C. The resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated to give the crude product, which was used in the next step without further purification (140 mg crude). MS (ESI) m/z 192.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-eb1a1ceb073248e6aad32d4a5f031b48
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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