Dimethylformamide → 2-[1-(4-chlorophenyl)cyclopropyl]-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

HRID 469556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469556
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11](=O)[CH:12]=[N+:13]=[N-:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.NN1[N:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:31].C(N(CC)CC)C.CN(C=[O:43])C>CCOC(C)=O.C([O-])(=O)C1C=CC=CC=1.[Ag+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11][C:12]([NH:13][N:14]3[N:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:31])=[O:43])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 671611112-amino-4-(trifluoromethyl)phthalazin-1(2H)-oneHCID 866537401-(1-(4-Chlorophenyl)cyclopropyl)-2-diazoethanone

Produkt 1

HCID 532379702-[1-(4-chlorophenyl)cyclopropyl]-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 164649Silver benzoateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of the above crude 1-(1-(4-chlorophenyl)cyclopropyl)-2-diazoethanone (0.050 g, 0.23 mmol), the product from Example 11B (0.0505 g, 0.22 mmol), triethylamine (0.12 mL, 0.86 mmol), and silver benzoate (0.0504 g, 0.220 mmol) in DMF (1 mL) were stirred for 2 hours at 70° C., diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (30% EtOAc/hexanes) to give the title compound (23.0 mg, 0.055 mmol) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 8.41-8.44 (m, 1H), 7.95-8.20 (m, 3H), 7.22-7.42 (m, 4H), 2.72 (d, J=1.0 Hz, 2H), 1.04-1.10 (m, 2H), 0.84-0.90 (m, 2H); MS (ESI+) M/Z 422 (M+H)+, 439 (M+NH4)+.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-82759220e557412299f75b2c3a4c038a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629143B2

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