4-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-9-thia-3-azabicyclo[3.3.1]nonane-2,4-dione

HRID 1253267노트

반응식

HRID 1253267 반응식
[S:1]1[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:2]1[CH2:3][CH2:4][CH2:5]2)=O.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[N:27][CH:26]=[C:25]([Cl:29])[N:24]=2)[CH2:19][CH2:18]1>C(Cl)Cl>[Cl:29][C:25]1[N:24]=[C:23]([N:20]2[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:12]3[C:7](=[O:9])[CH:6]4[S:1][CH:2]([CH2:3][CH2:4][CH2:5]4)[C:10]3=[O:11])[CH2:22][CH2:21]2)[CH:28]=[N:27][CH:26]=1

참가 물질

4

반응물 2

HCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amineHCID 54010570Tetrahydrothiopyran-2,6-dicarboxylic anhydride

생성물 1

HCID 141563753-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-9-thia-3-azabicyclo[3.3.1]nonane-2,4-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tetrahydrothiopyran-2,6-dicarboxylic anhydride (3.7 g., 21 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (5.63 g., 21 mmole) were combined in 200 ml. of methylene chloride and stirred for 30 minutes at room temperature. The solvent was removed in vacuum and 200 ml. of toluene added. The mixture was refluxed for 48 hours with water removal via a Dean-Stark trap. Upon cooling, the reaction was concentrated to an oil and this was dissolved in 2% ethanol/chloroform and filtered through silica gel. The fractions which contained the product were concentrated in vacuum and the resulting residue was recrystallized from isopropyl alcohol with the addition of 4N isopropanolic HCl. 0.6 Grams of the title compound was obtained as the hydrochloride, hydrate; m.p. 248°-250° C.

후처리

  1. customThe solvent was removed in vacuum and 200 ml
  2. additionof toluene added
  3. temperatureThe mixture was refluxed for 48 hours with water removal via a Dean-Stark trap
  4. temperatureUpon cooling
  5. concentrationthe reaction was concentrated to an oil
  6. dissolutionthis was dissolved in 2% ethanol/chloroform
  7. filtrationfiltered through silica gel
  8. concentrationwere concentrated in vacuum
  9. customthe resulting residue was recrystallized from isopropyl alcohol with the addition of 4N isopropanolic HCl

출처 및 근거

ORD 기록
ord-a0286dc6efa043949ddfecc8185664ec
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04748240

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