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

HRID 469557

反応式

HRID 469557 の反応式
[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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 671611112-amino-4-(trifluoromethyl)phthalazin-1(2H)-oneHCID 866537421-(1-(4-Chlorophenyl)cyclobutyl)-2-diazoethanone

生成物 1

HCID 532382012-[1-(4-chlorophenyl)cyclobutyl]-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)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)+.

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 (4% EtOAc/dichloromethane)

出典と根拠

ORDレコード
ord-67c07523bd4245a294c12a19b76207f6
出典データセット
uspto-grants-2014_01
特許番号
US08629143B2

関連ノート

読み込み中…