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

HRID 469557

Reaction equation

HRID 469557 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=O)[CH:13]=[N+:14]=[N-:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.NN1[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:32].C(N(CC)CC)C.CN(C=[O:44])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([CH2:12][C:13]([NH:14][N:15]3[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:32])=[O:44])[CH2:11][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 866537421-(1-(4-Chlorophenyl)cyclobutyl)-2-diazoethanone

Product 1

HCID 532382012-[1-(4-chlorophenyl)cyclobutyl]-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)cyclobutyl)-2-diazoethanone (65.6 mg, 0.280 mmol), the product from Example 11B (0.0503 g, 0.219 mmol), triethylamine (0.12 mL, 0.86 mmol), and silver benzoate (12.4 mg, 0.054 mmol) in DMF (1 mL) was stirred for 2 hours, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (4% EtOAc/dichloromethane) to give the title compound (33.5 mg) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.50 (s, 1H), 8.41 (dd, J=7.9, 1.4 Hz, 1H), 8.09-8.15 (m, 1H), 8.02-8.07 (m, 1H), 7.97-8.02 (m, 1H), 7.30-7.34 (m, 2H), 7.21-7.24 (m, 2H), 2.80 (s, 2H), 2.44-2.49 (m, 2H), 2.26-2.39 (m, 2H), 2.06-2.21 (m, 1H), 1.70-1.84 (m, 1H); MS (ESI+) M/Z 436 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-67c07523bd4245a294c12a19b76207f6
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Linked notes

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