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

HRID 450212

Reaktionsgleichung

Reaktionsgleichung von HRID 450212
[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]

Komponenten

7

Edukt 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)

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-54efd4be0aa445fc838534088bcc8497
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486954B2

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