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Pyridine → 2-[2-(3-chloro-pyridin-2-yl)-5-hydroxy-2H-pyrazol-3-yl]-10-methyl-3-oxa-1,8-diaza-phenanthren-4-one

HRID 245652
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인쇄 미리보기

반응식

HRID 245652 반응식
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:13]([OH:15])=[O:14].[Cl:16][C:17]1[C:18]([N:23]2[C:27]([C:28](O)=O)=[CH:26][C:25](C(F)(F)F)=[N:24]2)=[N:19][CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1.CS(Cl)(=O)=[O:43]>C1COCC1>[Cl:16][C:17]1[C:18]([N:23]2[C:27]([C:28]3[O:14][C:13](=[O:15])[C:3]4[C:4]5[C:9](=[N:8][CH:7]=[CH:6][CH:5]=5)[CH:10]=[C:11]([CH3:12])[C:2]=4[N:1]=3)=[CH:26][C:25]([OH:43])=[N:24]2)=[N:19][CH:20]=[CH:21][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 579901086-Amino-7-methyl-quinoline-5-carboxylic acid

생성물 1

HCID 1784223002-[2-(3-chloro-pyridin-2-yl)-5-hydroxy-2H-pyrazol-3-yl]-10-methyl-3-oxa-1,8-diaza-phenanthren-4-one수율 50.7%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 282 mg (1.39 mmol) of 6-amino-7-methyl-quinoline-5-carboxylic acid in 11 mL of anhydrous THF is added 407 mg (1.39 mmol) of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid followed by 560 μL (7.0 mmol) of pyridine. The mixture is stirred at ambient temperature during 30 minutes. Then the suspension is cooled to 0° C. and 430 μL (5.5 mmol) of methanesulfonyl chloride are added dropwise. The mixture is stirred at ambient temperature for 48 hours. Then the solvent is evaporated and the residue is sequentially triturated and filtrated with ethyl acetate and with a minimum of cold water. Purification of the residue by flash chromatography (SiO2, heptane/ethyl acetate 1:2) affords 286 mg (45%) of the product as a yellowish solid; LC/MS:468/460 (M+H)+.

후처리

  1. temperatureThen the suspension is cooled to 0° C.
  2. stirringThe mixture is stirred at ambient temperature for 48 hours
  3. customThen the solvent is evaporated
  4. customthe residue is sequentially triturated
  5. filtrationfiltrated with ethyl acetate and with a minimum of cold water
  6. customPurification of the residue by flash chromatography (SiO2, heptane/ethyl acetate 1:2)

출처 및 근거

ORD 기록
ord-06a5f9283694411d8b7c1cc70a110ade
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658801B2

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