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

HRID 1887558Notes

Reaction equation

HRID 1887558 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) m/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-24f2f0c502444ab6a6ee81ec167a21a2
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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