Potassium Carbonate → Ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1h-pyrazolo[3,4-b] pyridine-5-carboxylate

HRID 496596

반응식

HRID 496596 반응식
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=12.CN[S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].C([O-])([O-])=O.[K+].[K+].[CH3:36][N:37]1CCCC1=O>C1OCCOCCOCCOCCOCCOC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH2:36][NH:37][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=23)(=[O:21])=[O:22])=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 24400544-fluoro-N-methylbenzene-1-sulfonamideHCID 2736380ethyl 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

생성물 1

HCID 69733699Ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1h-pyrazolo[3,4-b] pyridine-5-carboxylate

시약·촉매·용매 1

HCID 2855718-Crown-6촉매

반응 조건

온도
100 °C

실험 절차

A mixture of 2.53 g (0.01 mol) of ethyl 4-chloro-1,3-dimethyl-1H pyrazolo[3,4-b]pyridine-5-carboxylate, 1.89 g (0.01 mol) of N-methyl-4-fluorobenzenesulfonamide, 6.91 g (0.05 mol) of anhydrous K2CO3, 0.143 g of 18-crown-6 and 70 ml of anhydrous 1-methyl-2-pyrrolidinone was stirred and heated at 100° C. for 17 hours. The solvent was removed under vacuum and water added to the residue. The mixture was extracted with CH2Cl2, and the extract washed with H2O, brine and dried (Na2SO4). The solution was filtered through a pad of hydrous magnesium silicate and the filtrate concentrated to dryness under vacuum to give 4.98 g of an oil. This oil was chromatographed on a silica gel column with ethyl acetate-hexane(2:3) as solvent to give 3.15 g of solid, mp 107-109° C.

후처리

  1. customThe solvent was removed under vacuum and water
  2. additionadded to the residue
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe extract washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationThe solution was filtered through a pad of hydrous magnesium silicate
  7. concentrationthe filtrate concentrated to dryness under vacuum

출처 및 근거

ORD 기록
ord-4b82875573834294837352ec2141a354
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06946473B2

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