Potassium Iodide → A-349821 free base

HRID 429239ノート

反応式

HRID 429239 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.Cl.[CH3:27][C@@H:28]1[CH2:32][CH2:31][C@@H:30]([CH3:33])[NH:29]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[CH3:27][C@@H:28]1[CH2:32][CH2:31][C@@H:30]([CH3:33])[N:29]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12268509(2R,5R)-2,5-dimethylpyrrolidine hydrochlorideHCID 155418504-{[4'-(3-Chloropropoxy)[1,1'-biphenyl]-4-yl]carbonyl}morpholine

生成物 1

HCID 9954017A-349821 free base収率 70%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

The product from Example 10E (30 mg, 0.084 mmol), (2R,5R)-2,5-dimethylpyrrolidine hydrochloride (50 mg, 0.5 mmol) (purchased from Toronto Research Chemicals, TRC), 75 mg of potassium carbonate and 75 mg of potassium iodide in 5 mL of 2-butanone were heated at 80° C. for 72 hours. The mixture was allowed to cool to ambient temperature, filtered and the filtrate was evaporated under reduced pressure. The residue was purified by HPLC chromatography (C18 reverse phase Water's 25 mm module prep column, 10 to 95% acetonitrile/0.1% TFA in water, 10 minute linear gradient, flow rate 40 mL/minute) to provide the title compound (70% yield).

後処理

  1. filtrationfiltered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by HPLC chromatography (C18 reverse phase Water's 25 mm module prep column, 10 to 95% acetonitrile/0.1% TFA in water, 10 minute linear gradient, flow rate 40 mL/minute)

出典と根拠

ORDレコード
ord-a88369258da74ae2954a32ed59707b7f
出典データセット
uspto-grants-2001_11
特許番号
US06316475B1

反応ノート

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