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

反応式

HRID 41571 の反応式
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

参加物

7

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ea0d1d88435b4ecf80e476d0423ae564
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

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