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

HRID 469556

反応式

HRID 469556 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 164649Silver benzoate触媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-82759220e557412299f75b2c3a4c038a
出典データセット
uspto-grants-2014_01
特許番号
US08629143B2

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