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

HRID 2198094노트

반응식

HRID 2198094 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 679Dimethyl Sulfoxide용매HCID 25517Ammonium Chloride용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-badfeb6fd5c24bc79935b5f7bb59dabd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338610B2

반응 노트

불러오는 중…