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

HRID 1514174ノート

反応式

HRID 1514174 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2d3070c81b0a4519a514eb1cf5899f9a
出典データセット
uspto-grants-2012_07
特許番号
US08222254B2

反応ノート

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