Pyridine → 7-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-5-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

HRID 245619노트

반응식

HRID 245619 반응식
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH3:14].[Br:15][C:16]1[CH:17]=[C:18]([C:28](O)=O)[N:19]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[N:20]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>C(#N)C>[Br:15][C:16]1[CH:17]=[C:18]([C:28]2[O:12][C:11](=[O:13])[C:10]3[C:2](=[C:3]([CH3:14])[CH:4]=[C:5]4[CH:6]=[N:7][NH:8][C:9]4=3)[N:1]=2)[N:19]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[N:20]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acidHCID 468557186-amino-5-methyl-2H-indazole-7-carboxylic acid

생성물 1

HCID 579901597-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-5-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a suspension of 700 mg (3.66 mmol) of 6-amino-5-methyl-1H-indazole-7-carboxylic acid in 26 mL of anhydrous acetonitrile is added 1.11 g (3.66 mmol) of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid followed by 1.3 mL (16.2 mmol) of pyridine. The mixture is stirred at ambient temperature during 30 minutes. Then the suspension is cooled to 0° C. and 1.0 mL (12.9 mmol) of methanesulfonyl chloride is added drop wise. The mixture is stirred at ambient temperature for 16 hours. Then the solvent is evaporated and the residue is triturated with a minimum of cold water. The precipitate, which is formed is filtrated, washed with cold water and dried. The pale yellowish product obtained (1.6 g) is engaged in the next step; LC/MS:459/461 (M+H)+.

후처리

  1. temperatureThen the suspension is cooled to 0° C.
  2. stirringThe mixture is stirred at ambient temperature for 16 hours
  3. customThen the solvent is evaporated
  4. customthe residue is triturated with a minimum of cold water
  5. customThe precipitate, which is formed
  6. filtrationis filtrated
  7. washwashed with cold water
  8. customdried
  9. customThe pale yellowish product obtained (1.6 g)

출처 및 근거

ORD 기록
ord-3a22f39a7a37423cad5e31ce3d568b26
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658801B2

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