Pyrazole → HCID 68153941, 화합물

HRID 341081

반응식

HRID 341081 반응식
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2=[N:20][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:22](=[O:23])[C:12]2=[CH:11]1.[NH:31]1[CH:35]=[CH:34][CH:33]=[N:32]1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.CS(C)=O>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[N:21]1[C:22](=[O:23])[C:12]2=[CH:11][N:10]([CH2:9][C:3]3[CH:4]=[CH:5][C:6]([N:31]4[CH:35]=[CH:34][CH:33]=[N:32]4)=[CH:7][C:2]=3[F:1])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]2=[N:20]1

참가 물질

7

반응물 4

HCID 1048PyrazoleHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 671125025-[(2-fluoro-4-iodophenyl)methyl]-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazol[4,3-c]quinolin-3-one

생성물 1

HCID 68153941HCID 68153941, 화합물

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

5-[(2-Fluoro-4-iodophenyl)methyl]-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazol[4,3-c]quinolin-3-one [(Example 187, Step 2), 68 mg, 0.13 mmol], pyrazole (18 mg, 0.26 mmol, 2 equiv) and copper(I) iodide (10 mg, 0.053 mmol, 0.4 equiv) were combined in a sealed tube, to which was added dimethylsulfoxide (1 mL), (±)-trans-N,N′-bismethyl-1,2-cyclohexane diamine (15 mg, 0.11 mmol, 0.8 equiv) and an aqueous (0.2 ml) solution of potassium phosphate (84 mg, 0.40 mmol, 3 equiv). The vessel was flushed with nitrogen, sealed and placed into a preheated oil bath at 100° C. for 1 hour. The mixture was cooled to ambient temperature, poured into water (15 mL) and extracted with chloroform (2×15 mL). The combined organic extracts were washed once with water (5 mL) and brine (5 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.09 (1H, s), 8.54 (1H, d, J=2.6 Hz), 8.21 (1H, dd, J=7.9, 1.5 Hz), 7.82 (1H, dd, J=11.9, 2.1 Hz), 7.73-7.73 (2H, m), 7.68-7.59 (3H, m), 7.55 (1H, t, J=7.6 Hz), 7.49-7.32 (4H, m), 6.56 (1H, dd, J=2.3, 2.0 Hz), 5.82 (2H s) ppm; high resolution mass spectrometry (ES+) m/z 454.1467 [(M+H)+; calculated for C26H18F2N5O: 454.1474].

후처리

  1. customThe vessel was flushed with nitrogen
  2. customsealed
  3. additionpoured into water (15 mL)
  4. extractionextracted with chloroform (2×15 mL)
  5. washThe combined organic extracts were washed once with water (5 mL) and brine (5 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; chloroform:methanol)

출처 및 근거

ORD 기록
ord-e5ea697f64c7486c9136aad50841e614
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895580B2

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