Water → N-Methyl-4-((2-(methylthio)benzo[d]thiazol-6-yl)oxy)picolinamide

HRID 1922219

반응식

HRID 1922219 반응식
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:13][NH:14][C:15]([C:17]1[CH:22]=[C:21](Cl)[CH:20]=[CH:19][N:18]=1)=[O:16].O>CN(C=O)C>[CH3:13][NH:14][C:15]([C:17]1[CH:22]=[C:21]([O:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:3]([S:2][CH3:1])[S:4][C:5]=3[CH:11]=2)[CH:20]=[CH:19][N:18]=1)=[O:16]

참가 물질

5

반응물 3

HCID 962WaterHCID 14768144-Chloro-N-methylpicolinamideHCID 450774142-(Methylsulfanyl)-1,3-benzothiazol-6-ol

생성물 1

HCID 57725401N-Methyl-4-((2-(methylthio)benzo[d]thiazol-6-yl)oxy)picolinamide수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To the solution of 2-methylsulfanyl-benzothiazol-6-ol (3.76 g, 19.08 mmol, 1.0 eq) in DMF (25 mL), was added CsCO3 (15.54 g, 47.70 mmol, 2.5 eq) at room temperature. After stirring for a while, 4-chloro-pyridine-2-carboxylic acid methylamide (4.86 g, 28.62 mmol, 1.5 eq) was added to the mixture and the mixture was stirred at 70° C. under reflux condenser overnight. After cooling the reaction mixture in ice bath, water (100 mL) was added and the aqueous layer was extracted with ethyl acetate (3×150 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo. The crude product was purified using 20 g of ISCO Silica Gel column (0%-50%-80%-100% ethyl acetate-hexane mixture over 45 min 40 mL/min run) to yield 4-(2-methylsulfanyl-benzothiazol-6-yloxy)-pyridine-2-carboxylic acid methylamide (3.88 g, 62%) as a white solid. M+H=332.1

후처리

  1. additionwas added to the mixture
  2. temperatureunder reflux condenser overnight
  3. temperatureAfter cooling the reaction mixture in ice bath
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×150 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified
  9. custom20 g of ISCO Silica Gel column (0%-50%-80%-100% ethyl acetate-hexane mixture over 45 min 40 mL/min run)

출처 및 근거

ORD 기록
ord-331f32a309454680bb5f7343db8cc8f0
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173689B2

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