Potassium Iodide → 6-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1634188노트

반응식

HRID 1634188 반응식
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[N:11]=[C:12]([CH3:14])[S:13][C:7]2=[N:6][C:5]=1[CH3:15].[CH2:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:21][C:20]=2[CH2:19][CH2:18][NH:17]1.C(=O)(O)[O-].[Na+].[I-].[K+]>C(O)CCC>[CH2:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:21][C:20]=2[CH2:19][CH2:18][N:17]1[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[N:11]=[C:12]([CH3:14])[S:13][C:7]2=[N:6][C:5]=1[CH3:15]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 7232301H,2H,3H,4H,5H-pyrido[4,3-b]indoleHCID 155864606-(2-chloroethyl)-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

생성물 1

HCID 186774246-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one수율 28.1%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 6-(2-chloroethyl)-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (4.2 g), 1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indole (2.65 g), sodium bicarbonate (2 g), potassium iodide (0.1 g) in 1-butanol (122 ml) was refluxed for 20 hours. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3/CH3OH 95/5). The solvent of the desired fraction was evaporated and the residue was crystallized from acetonitrile, yielding 1.6 g (28.1%) of 6-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (compound 42).

후처리

  1. temperaturewas refluxed for 20 hours
  2. filtrationThe reaction mixture was filtered while hot and the filtrate
  3. customwas evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3/CH3OH 95/5)
  5. customThe solvent of the desired fraction was evaporated
  6. customthe residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-75d9d18af57b4bf9a4998581fece5a7e
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506768B2

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