Isopropylamine → 3-Amino-N-isopropyl-5-(trifluoromethyl)benzamide

HRID 884522Notes

Reaction equation

HRID 884522 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=O.C1C=C[C:18]2N(O)N=[N:21][C:19]=2[CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC(N)C.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([NH:21][CH:19]([CH3:20])[CH3:18])=[O:7]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6095563-Amino-5-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 593946503-Amino-N-isopropyl-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-5-(trifluoromethyl)benzoic acid (0.25 g, 1.22 mmol) in DMF (3 mL) is added HOBt (0.494 g, 3.66 mmol) followed by HATU (0.695 g, 1.83 mmol), propan-2-amine (0.311 mL, 3.66 mmol) and DIEA (0.96 mL, 5.48 mmol). After stirring at it overnight the solution is concentrated and the residue is dissolved in EtOAc, washed with sat aq NaHCO3, brine, and dried over Na2SO4. Following concentration the residue is carried on to next step without further purification. MS (ESI) ni/z 247.1 (M+1).

Workup

  1. concentrationis concentrated
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed with sat aq NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentration the residue
  6. customis carried on to next step without further purification

Sources & evidence

ORD record
ord-901b1e581d3045b7acf4f39353582078
Source dataset
uspto-grants-2012_08
Patent number
US08242125B2

Reaction notes

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