Triethylamine → n-[2-Methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1h-pyrazole-5-carboxamide

HRID 516503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516503
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:7]=[C:6]([C:8](O)=[O:9])[N:5]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[N:4]=1.[NH2:23][C:24]1[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][C:25]=1[C:26]([NH:28][CH:29]([CH3:31])[CH3:30])=[O:27].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl-].C(N(CC)CC)C>C(#N)C>[CH3:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:25]([C:26]([NH:28][CH:29]([CH3:30])[CH3:31])=[O:27])[C:24]=1[NH:23][C:8]([C:6]1[N:5]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[N:4]=[C:3]([C:2]([F:21])([F:1])[F:22])[CH:7]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 167760932-amino-3-methyl-N-(1-methylethyl)benzamideHCID 222503263-(Trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1h-pyrazole-5-carboxylic acidHCID 131720136BOP chloride

Produkt 1

HCID 22250330n-[2-Methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1h-pyrazole-5-carboxamideAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of the title compound of Example 3, Step B (0.54 g, 1.1 mmol), the title compound from Example 1, Step B (0.44 g, 2.4 mmol) and BOP chloride (bis(2-oxo-oxazolidinyl)phosphinyl chloride, 0.54 g, 2.1 mmol) in acetonitrile (13 mL) was treated with triethylamine (0.9 mL). The mixture was shaken in a closed scintillation vial for 18 h. The reaction was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid. The ethyl acetate layer was washed successively with 1N hydrochloric acid (50 mL), 1N sodium hydroxide (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel with hexanes/ethyl acetate (5:1 to 3:1) as eluent. The title compound (0.43 g), a compound of the present invention, was isolated as a white solid. m.p. 277-230° C.

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid
  2. washThe ethyl acetate layer was washed successively with 1N hydrochloric acid (50 mL), 1N sodium hydroxide (50 mL) and saturated sodium chloride solution (50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-514fd6791f5f4d45abe046ab840260d2
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09113630B2

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