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

HRID 469557

반응식

HRID 469557 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 532382012-[1-(4-chlorophenyl)cyclobutyl]-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

시약·촉매·용매 2

HCID 164649Silver benzoate촉매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-67c07523bd4245a294c12a19b76207f6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629143B2

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