Potassium Phosphate, Tribasic → 2-(3-(2H-1,2,3-triazol-2-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41571

반응식

HRID 41571 반응식
I[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C:8]2([CH2:16][CH2:15][N:14]([C:17]3[CH:26]=[N:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[CH2:13][CH2:12]2)[C:7]1=[O:27].[NH:31]1[CH:35]=[CH:34][N:33]=[N:32]1.CN[C@@H]1CCCC[C@H]1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[N:31]1[N:32]([C:2]2[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=2)[CH2:5][N:6]2[CH2:11][CH2:10][CH2:9][C:8]3([CH2:16][CH2:15][N:14]([C:17]4[CH:26]=[N:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:18]=4)[CH2:13][CH2:12]3)[C:7]2=[O:27])[N:33]=[CH:34][CH:35]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 672520422-(3-Iodobenzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneHCID 178418936HCID 178418936, 화합물

생성물 1

HCID 532597882-(3-(2H-1,2,3-triazol-2-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 30.9%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

To a mixture of 2-(3-iodobenzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (104 mg, 0.20 mmol), 1H-1,2,3-triazole (28 mg, 0.40 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine [68737-65-5] (6 mg, 0.04 mmol) and K3PO4 (127 mg, 0.60 mmol) in DMF (2 mL), CuI (15 mg, 0.08 mmol) was added and the reaction mixture was stirred at 110° C. for 24 h. The reaction mixture was cooled to it and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by reversed phase preparative HPLC (column AG/PP/C-18-15/025, flow 20 mL/min, mobile phase water (A): acetonitrile (B) gradient) to yield the regioisomeric title compounds (example 8: 28 mg, 31% and example 9: 54 mg, 60%).

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to it
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by reversed phase preparative HPLC (column AG/PP/C-18-15/025, flow 20 mL/min, mobile phase water (A): acetonitrile (B) gradient)

출처 및 근거

ORD 기록
ord-ea0d1d88435b4ecf80e476d0423ae564
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

연결된 노트

불러오는 중…