Methyl iodide → 4-(Cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514174노트

반응식

HRID 1514174 반응식
[CH3:1]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH:19]1([CH2:25][N:26]2[C:30]([CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][N:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[O:45][CH3:46])[CH2:35][CH2:34]3)=[N:29][NH:28][C:27]2=[O:47])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.CI>CC#N.C(Cl)Cl>[CH:19]1([CH2:25][N:26]2[C:30]([CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][N:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[O:45][CH3:46])[CH2:37][CH2:38]3)=[N:29][N:28]([CH3:1])[C:27]2=[O:47])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 251844534-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 251847974-(Cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one수율 82.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a slurry of PS-BEMP (0.95 g, 2.08 mmol, 2.2 mmol/g) and 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (E17; 415 mg, 1.028 mmol) in MeCN (20 mL), methyl iodide (0.13 mL, 2.08 mmol) was added and the reaction mixture was stirred at room temperature for 2 days. The resin was filtered, washed with MeOH (25 mL) and the solvent was evaporated in vacuo to afford 560 mg crude yellow glassy solid. This was dissolved in DCM (3 mL) and purified by flash chromatography (Flash Master, Biotage Isolute SI, 20 g column, gradient 0-10% MeOH in DCM over 30 min) to afford 350 mg of a light yellow oil. Further purification by preparative LC-MS afforded 190 mg (44%) of the title compound as a glassy solid.

후처리

  1. filtrationThe resin was filtered
  2. washwashed with MeOH (25 mL)
  3. customthe solvent was evaporated in vacuo
  4. customto afford 560 mg crude yellow glassy solid
  5. custompurified by flash chromatography (Flash Master, Biotage Isolute SI, 20 g column, gradient 0-10% MeOH in DCM over 30 min)

출처 및 근거

ORD 기록
ord-2d3070c81b0a4519a514eb1cf5899f9a
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222254B2

반응 노트

불러오는 중…