4-Methylmorpholine → (1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazol-4-yl)-[4-(1-methyl-piperidin-4-ylmethyl)-piperazin-1-yl]-methanone

HRID 1011887ノート

反応式

HRID 1011887 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]([N:16]3[C:20]([CH2:21][CH3:22])=[C:19]([C:23](O)=[O:24])[C:18]([CH2:26][CH3:27])=[N:17]3)[CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH3:46][N:47]1[CH2:52][CH2:51][CH:50]([CH2:53][N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:49][CH2:48]1>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]([N:16]3[C:20]([CH2:21][CH3:22])=[C:19]([C:23]([N:57]4[CH2:56][CH2:55][N:54]([CH2:53][CH:50]5[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]5)[CH2:59][CH2:58]4)=[O:24])[C:18]([CH2:26][CH3:27])=[N:17]3)[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 673139751-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid2 回

生成物 1

HCID 57554975(1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazol-4-yl)-[4-(1-methyl-piperidin-4-ylmethyl)-piperazin-1-yl]-methanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 0.40 g (1.10 mmol) of 1-{3-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid (intermediate 1) and 0.18 g (1.1 mmol) of 2-chloro-4,6-dimethoxy-[1,3,5]triazine were dissolved in 10 ml of MeCN. The solution was then cooled down to 0° C. and 0.32 g=0.35 ml (3.2 mmol) of N-methylmorpholine was added drop by drop. After 2 hours stirring at 0° C., a solution of 0.21 g (1.1 mmol) 1-(1-methyl-piperidin-4-ylmethyl)-piperazine in 3 ml of MeCN was added drop by drop. Then, the mixture was warmed up to RT and stirring continued for 20 hours. Subsequently, it was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0-7.5:2.5) to afford the title compound as colorless solid. MS: 560.2 (MH+, 1 Cl).

後処理

  1. temperatureThen, the mixture was warmed up to RT
  2. stirringstirring
  3. waitcontinued for 20 hours
  4. additionSubsequently, it was poured
  5. extractionextracted twice with EtOAc
  6. washthe organic phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0-7.5:2.5)

出典と根拠

ORDレコード
ord-3cd2c10fc5c24237a856c05cb19d8ee3
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

反応ノート

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