Trifluoroacetic acid → 3-(aminomethyl)-N-(4'-fluoro-4-nitro-[1,1'-biphenyl]-3-yl)azetidine-1-carboxamide

HRID 2201713Notes

Reaction equation

HRID 2201713 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([NH:17][C:18]([N:20]3[CH2:23][CH:22]([CH2:24][NH:25]C(=O)OC(C)(C)C)[CH2:21]3)=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:25][CH2:24][CH:22]1[CH2:21][N:20]([C:18]([NH:17][C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:13]=[CH:12][C:11]=2[N+:14]([O-:16])=[O:15])=[O:19])[CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71007318Tert-butyl (1-(4'-fluoro-4-nitrobiphenyl-3-ylcarbamoyl)azetidin-3-yl)methylcarbamate

Product 1

HCID 709825763-(aminomethyl)-N-(4'-fluoro-4-nitro-[1,1'-biphenyl]-3-yl)azetidine-1-carboxamideYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-(4′-fluoro-4-nitrobiphenyl-3-ylcarbamoyl)azetidin-3-yl)methylcarbamate (2.0 g, 4.5 mmol) in DCM (60 mL) was added TFA (8 mL, 104 mmol) at 0° C. The reaction was warmed to room temperature and stirred for 2 h. The reaction was then concentrated under reduced pressure. The residue was basified with a saturated aqueous solution of NaHCO3 and extracted with a 15% MeOH in DCM. The organic layer was dried over Na2SO4 and concentrated to afford 3-(aminomethyl)-N-(4′-fluoro-4-nitro-[1,1′-biphenyl]-3-yl)azetidine-1-carboxamide (1.6 g, 100% yield) as yellow syrup which is used in the next step as such without any further purification.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. extractionextracted with a 15% MeOH in DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-17c3c78749cc4bf8b4d11769347d9de2
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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