Water → HCID 57227886, 화합물

HRID 357030

반응식

HRID 357030 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[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[C:22]1[S:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].O>CN(C)C=O>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[C:22]1[S:26][C:25](=[O:27])[N:24]([CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[C:23]1=[O:28]

참가 물질

5

반응물 3

HCID 962WaterHCID 36416932,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-HCID 18936641Imidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-

생성물 1

HCID 57227886HCID 57227886, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1.81 g (7.5 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 1.59 g (7.5 mmol) of 5-(2-thienylmethylene)thiazolidine-2,4-dione in 70 ml of N,N-dimethylformamide, 1.12 ml (7.5 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, hexane/ethyl acetate=2/1→1/1→ethyl acetate). The resulting crude crystal was purified by recrystallization (solvent, chloroform/diethyl ether) to yield 1.54 g (49.5%, light yellow crystal) of the desired product.m.p. 116.0°-117.0° C.; 1H-NMR (CDCl3, 200 MHz) δ 1.64-1.92 (4H, m), 3.03 (2H, t, J=7.0 Hz), 3.76 (2H, t, J=7.0 Hz), 6.92 (1H, dd, J=1.0, 7.0 Hz), 7.15 (1H, dd, J=7.2, 9.2 Hz), 7.21 (1H, dd, J=3.8, 5.2 Hz), 7.42 (1H, d, J=3.6 Hz), 7.58 (1H, d, J=9.0 Hz), 7.68 (1H, d, J=5.0 Hz), 7.70 (1H, d, J=1.4 Hz), 7.85 (1H, s), 8.05 (1H, s); IR (KBr) 1728, 1678, 1599, 1369, 1128, 773, 727 cm-1 ; Anal. Calcd for C19H17N3O2S3 : C, 54.92; H, 4.12; N, 10.11. Found: C, 54.67, H, 4.18; N, 10.03

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, hexane/ethyl acetate=2/1→1/1→ethyl acetate)
  7. customThe resulting crude crystal was purified by recrystallization (solvent, chloroform/diethyl ether)

출처 및 근거

ORD 기록
ord-62d37ea2ee774ab8a631b79813a27a4e
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840732

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