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

HRID 469556

Reaction equation

HRID 469556 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 164649Silver benzoateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-82759220e557412299f75b2c3a4c038a
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Linked notes

Loading…