O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-(3-Amino-2,4-dichloro-benzyl)-2-methyl-2-fluoro-propionamide

HRID 1189625Notes

Reaction equation

HRID 1189625 reaction equation
[F:1][C:2]([CH3:7])([CH3:6])[C:3](O)=[O:4].[NH2:8][C:9]1[C:10]([Cl:18])=[C:11]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:12][NH2:13].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[NH2:8][C:9]1[C:10]([Cl:18])=[C:11]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:12][NH:13][C:3](=[O:4])[C:2]([CH3:7])([F:1])[CH3:6]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27828282-Fluoro-2-methylpropanoic acidHCID 568399683-(Aminomethyl)-2,6-dichloroaniline

Product 1

HCID 67957110N-(3-Amino-2,4-dichloro-benzyl)-2-methyl-2-fluoro-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-fluoroisobutyric acid (555 mg, 5.2 mmol), 3-amino-2,4-dichloro-benzylamine (1.00 g, 5.2 mmol), TBTU (1.85 g, 5.8 mmol), TEA (1.82 mL, 13 mmol) and THF is stirred at rt overnight. The mixture is concentrated, stirred with sat. aq NaHCO3-solution and the resulting precipitate is collected by filtration, washed with water and dried.

Workup

  1. concentrationThe mixture is concentrated
  2. stirringstirred with sat. aq NaHCO3-solution
  3. filtrationthe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f299b01f2c1343d79873e57443087ce6
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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