N,N'-Dimethylethylenediamine → 1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (6-methanesulfonyl-pyridin-3-ylmethyl)-amide

HRID 2198094ノート

反応式

HRID 2198094 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:20]=[N:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:14]=3[CH:15]=[N:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.[CH3:28][S:29]([O-:31])=[O:30].[Na+].CNCCNC.CCOC(C)=O>CS(C)=O.[Cl-].[NH4+].FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[CH3:28][S:29]([C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:20]=[N:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:14]=3[CH:15]=[N:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1)(=[O:31])=[O:30]

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 8857Ethyl AcetateHCID 2733271Sodium methanesulfinateHCID 451380091-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid(6-bromopyridin-3-ylmethyl)-amide

生成物 1

HCID 451380101-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (6-methanesulfonyl-pyridin-3-ylmethyl)-amide

試薬・触媒・溶媒 3

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
110 °C

実験手順

To a microwave tube charged with 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (6-bromopyridin-3-ylmethyl)-amide (62 mg, 0.15 mmol) in DMSO (1 mL) was added copper (II) trifluoromethanesulfonate (53 mg, 0.15 mmol), sodium methanesulfinate (24 mg, 0.24 mmol) and N,N′ dimethylethylene diamine (47 μL, 0.44 mmol). The mixture was warmed at 110° C. for 45 minutes in the microwave. The reaction was monitored by TLC (EtOAc). The reaction was the diluted with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (4×7 mL). The combined organic layers were washed with saturated aqueous ammonium chloride (3×7 mL), brine (7 mL), aqueous K2CO3 (7 mL), brine (7 mL), dried over magnesium sulfate, filtered and concentrated. The solid was triturated with ether to afford the title compound.

後処理

  1. extractionextracted with EtOAc (4×7 mL)
  2. washThe combined organic layers were washed with saturated aqueous ammonium chloride (3×7 mL), brine (7 mL), aqueous K2CO3 (7 mL), brine (7 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid was triturated with ether

出典と根拠

ORDレコード
ord-badfeb6fd5c24bc79935b5f7bb59dabd
出典データセット
uspto-grants-2012_12
特許番号
US08338610B2

反応ノート

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