Water → 3-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357001

반응식

HRID 357001 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[S:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:15]1[CH:14]=[CH:13][N:12]2[C:7]([S:6][CH2:5][CH2:4][CH2:3][CH2:2][N:18]3[C:19](=[O:21])[CH2:20][S:16][C:17]3=[O:22])=[CH:8][CH:9]=[CH:10][C:11]=12

참가 물질

6

반응물 4

HCID 962WaterHCID 5437ThiazolidinedioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18936641Imidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-

생성물 1

HCID 189366943-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 8.35 g (35.4 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 4.15 g (35.4 mmol) of thiazolidine-2,4-dione in 200 ml of N,N-dimethylformamide, 5.30 ml (35.4 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by heating at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate). The resulting crude crystal was purified by recrystallization (solvent: chloroform/diethyl ether) to yield 10.01 g (88.0%, light orange crystal) of the desired product.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)
  7. customThe resulting crude crystal was purified by recrystallization (solvent: chloroform/diethyl ether)

출처 및 근거

ORD 기록
ord-52a73c16fc07454983d12e6504b1120c
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840732

연결된 노트

불러오는 중…