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

HRID 357062

반응식

HRID 357062 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.[NH:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[O:18].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:19]3[C:20](=[O:21])[CH2:22][NH:16][C:17]3=[O:18])=[CH:8][CH:9]=[CH:10][C:11]=12

참가 물질

6

반응물 4

HCID 962WaterHCID 10006HydantoinHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18936641Imidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-

생성물 1

HCID 189366653-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]hydantoin

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of 2.41 g (10.0 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 1.00 g (10.0 mmol) of hydantoin in 30 ml of N,N-dimethylformamide, 1.50 ml (10.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80° C. for 16 hours. After the reaction mixture was cooled, water was added; the mixture was extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=20/1→10/1) to yield 1.27 g (41.7%, yellow solid) of the desired product.

후처리

  1. temperatureAfter the reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. customdried
  4. distillationafter which the solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent, chloroform/methanol=20/1→10/1)

출처 및 근거

ORD 기록
ord-356bb265275d412ca0d7a303c808ed76
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840732

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