Hydrochloric Acid → N-[4-chloro-3-(trifluoromethyl)phenyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 1640165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640165
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([C:13]([OH:15])=O)[CH2:10]2)=[CH:5][CH:4]=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[C:24]([F:27])([F:26])[F:25].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:13]([CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)=[O:15])=[CH:19][C:18]=1[C:24]([F:25])([F:26])[F:27]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 147228197-Methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Produkt 1

HCID 58902339N-[4-chloro-3-(trifluoromethyl)phenyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamideAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (250 mg, 1.21 mmol), and 4-chloro-3-(trifluoromethyl)aniline (260 mg, 1.33 mmol) in DMF (12.0 mL) was added DIPEA (1.06 mL, 6.07 mmol) and then HATU (508 mg, 1.34 mmol). The solution was allowed to stir at rt for 18 h. 1N HCl was added and the mixture was extracted with EtOAc. The organic solution was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography to give N-[4-chloro-3-(trifluoromethyl)phenyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide as a white solid (233 mg, 50%). LCMS: (FA) ES+ 384.1, ES− 382.1.

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic solution was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ae9d3c480e44fae87c0559ce8ca48f1
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110687B2

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