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4-Methylmorpholine → 3-(4'-Chlorobiphenyl-4-yl)propynoic acid-[4-(4-methylpiperazin-1-ylmethyl)phenyl]amide

HRID 735043
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HRID 735043 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=2)[CH2:37][CH2:36]1>C1COCC1>[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:16](=[O:18])[C:15]#[C:14][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[CH:13][CH:12]=3)=[CH:44][CH:43]=2)[CH2:37][CH2:36]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 68816492(4'-Chlorobiphenyl-4-yl)propynoic acid

생성물 1

HCID 578457233-(4'-Chlorobiphenyl-4-yl)propynoic acid-[4-(4-methylpiperazin-1-ylmethyl)phenyl]amide

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A solution of 0.26 g (1 mmol) of (4′-chlorobiphenyl-4-yl)propynoic acid and 0.12 mL (1.1 mmol) of N-methylmorpholine in 20 mL of absolute THF is combined at −15° C. with 0.14 mL (1.1 mmol) of isobutyl chloroformate and stirred for ten minutes. Then 0.226 g (1.1 mmol) of 4-(4-methylpiperazin-1-ylmethyl)phenylamine dissolved in 7 mL of THF is added and the reaction mixture is stirred for 2 hours until ambient temperature is reached. The reaction mixture is evaporated down and the residue is dissolved in dichloromethane. The organic phase is washed twice with water and then dried over sodium sulfate. The desiccant is filtered off and the solvent is distilled off. The residue is triturated with ether and suction filtered. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia (90/10/0.1)). Yield: 60 mg (14% of theory); melting point: 182° C.-185° C.; C27H26ClN3O (M=443.97); calc.: molecular ion peak (M+H)+: 444/446 (Cl); found: molecular ion peak (M+H)+: 444/446 (Cl); Rf value: 0.4 (silica gel, dichloromethane/methanolic ammonia (90:10:0.1)).

후처리

  1. additionis added
  2. stirringthe reaction mixture is stirred for 2 hours until ambient temperature
  3. customThe reaction mixture is evaporated down
  4. dissolutionthe residue is dissolved in dichloromethane
  5. washThe organic phase is washed twice with water
  6. dry with materialdried over sodium sulfate
  7. filtrationThe desiccant is filtered off
  8. distillationthe solvent is distilled off
  9. customThe residue is triturated with ether and suction
  10. filtrationfiltered
  11. customThe purification

출처 및 근거

ORD 기록
ord-1eae23011e644a289f62901cefc36a47
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592373B2

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