Trifluoroacetic acid → 1-Amino-N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]cyclopropanecarboxamide

HRID 2068556Notes

Reaction equation

HRID 2068556 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:28]=[CH:27][CH:26]=[CH:25][C:7]=3[CH2:8][CH2:9][C@@H:10]([NH:11][C:12]([C:14]3([NH:17]C(=O)OC(C)(C)C)[CH2:16][CH2:15]3)=[O:13])[C:4]2=[N:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:17][C:14]1([C:12]([NH:11][C@@H:10]2[CH2:9][CH2:8][C:7]3[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=3[N:5]3[CH:1]=[CH:2][N:3]=[C:4]23)=[O:13])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67234396Tert-butyl N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]carbamate

Product 1

HCID 583040891-Amino-N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]cyclopropanecarboxamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve tert-butyl N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]carbamate (856 mg, 2.24 mmol) in dichloromethane (20 mL) and cool in an ice bath. Add trifluoroacetic acid (10 mL, 132.25 mmol). Remove the bath and stir the reaction for 1 hr. Concentrate the mixture under reduced pressure and add ethyl acetate. Wash with 1N NaOH and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure to give the title compound (470 mg, 74%) as a white solid: MS (m/z): 283 (M+1).

Workup

  1. temperaturecool in an ice bath
  2. customRemove the bath
  3. customthe reaction for 1 hr
  4. concentrationConcentrate the mixture under reduced pressure
  5. additionadd ethyl acetate
  6. washWash with 1N NaOH and brine
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate the organic layer under reduced pressure

Sources & evidence

ORD record
ord-42f1547227c2440a868be047d2955629
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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