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

HRID 469556

반응식

HRID 469556 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 532379702-[1-(4-chlorophenyl)cyclopropyl]-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)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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-82759220e557412299f75b2c3a4c038a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629143B2

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