تفاعل #792154

ord-4530a2f0d4864f338781a44ed00da8b8

معادلة التفاعل

O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1C(F)(F)F
title compound
O=C(O)c1cc(C(F)(F)F)nn1-c1ncccc1C(F)(F)F
3-(Trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1H-pyrazole-5-carboxylic acid
Cc1cccc(C(=O)NC(C)C)c1N
title compound
Cc1cccc(C(=O)NC(C)C)c1N
2-Amino-3-methyl-N-(1-methylethyl)benzamide
CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F.[Cl-]
BOP chloride
CCN(CC)CC
triethylamine
Cc1cccc(C(=O)NC(C)C)c1NC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1C(F)(F)F
title compound
المردود 78.3%
Cc1cccc(C(=O)NC(C)C)c1NC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1C(F)(F)F
N-[2-Methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1H-pyrazole-5-carboxamide
المردود 78.3%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid
  2. 2
    غسيلThe 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. 3
    تجفيفThe organic layer was dried over magnesium sulfate
  4. 4
    تركيزconcentrated

الإجراء التجريبي

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. 227-230° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09173400B2uspto-grants-2015_11