Potassium Iodide → 5-{3-[4-(5-Cyanoindol-3-yl)-1,2,5,6-tetrahydropyrid-1-yl]propoxy}-2-methylbenzothiazole

HRID 1016506

반응식

HRID 1016506 반응식
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14]Cl)=[CH:7][C:5]=2[N:6]=1.[C:16]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[C:27]1[CH2:28][CH2:29][NH:30][CH2:31][CH:32]=1)#[N:17].[I-].[K+]>C(#N)C.O.[OH-].[NH4+].C(OCC)(=O)C>[C:16]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[C:27]1[CH2:28][CH2:29][N:30]([CH2:14][CH2:13][CH2:12][O:11][C:8]2[CH:9]=[CH:10][C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH:7]=2)[CH2:31][CH:32]=1)#[N:17]

참가 물질

8

반응물 3

HCID 4875Potassium IodideHCID 113335543-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrileHCID 184070592-Methyl-5-(3-chloropropoxyl)-benzothiazole

생성물 1

HCID 102028485-{3-[4-(5-Cyanoindol-3-yl)-1,2,5,6-tetrahydropyrid-1-yl]propoxy}-2-methylbenzothiazole수율 37.6%

시약·촉매·용매 4

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매HCID 14923Ammonium Hydroxide용매

실험 절차

A mixture of 2-methyl-5-(3-chloropropoxyl)-benzothiazole (3 g, 12.4 mmol), 5-cyano-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (3 g, 13.4 mmol) and a catalytic amount of potassium iodide in 50 ml of acetonitrile was stirred at 80° C. overnight. The reaction mixture was cooled, diluted with water, ammonium hydroxide and ethyl acetate. The two phases were separated and the aqueous phase was extracted with ethyl acetate twice. The organic phases were combined, washed with brined, dried over sodium sulfate and then concentrated under reduced pressure to a solid. This residual solid was subjected to a silica gel chromatography, eluting with 7% methanol in dichloromethane. Fractions shown to contain product were combined and concentrated to provide 2 g of the title compound in 35% yield as free base. The resulting free base was dissolved in methanol/dichloromethane and precipitated with excess HCl in ether. Recrystalization from ethanol give 1.8 g of the title compound as a light yellow solid. mp. 263-65° C. MS(CI) m+1=429. EA (C25H24N4 OS.1.7HCl): Theory: C, 61.21%; H, 5.28%; N, 11.42%. Found: C, 61.10%; H, 5.43%; N, 11.39%.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customThe two phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate twice
  4. washwashed with brined,
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure to a solid
  7. washeluting with 7% methanol in dichloromethane
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1a07a0b309bc413491f7967027a90f80
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476051B2

연결된 노트

불러오는 중…