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 380381ノート

反応式

HRID 380381 の反応式
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]

参加物

6

反応物 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

生成物 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-one収率 28.1%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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-(l,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).

後処理

  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

出典と根拠

ORDレコード
ord-f892da1676604a2880ddc6e90d8fd537
出典データセット
uspto-grants-2001_10
特許番号
US06303614B1

反応ノート

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