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

HRID 496596

反応式

HRID 496596 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2855718-Crown-6触媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b82875573834294837352ec2141a354
出典データセット
uspto-grants-2005_09
特許番号
US06946473B2

関連ノート

読み込み中…