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Dimethylformamide → Morpholine-4-carboxylic acid {4-[2-methyl-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

HRID 492785
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 492785
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:11][C:12]#[N:13].[K+].[NH2:15][C:16]1[CH:37]=[CH:36][C:19]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])[CH:22]=2)=[C:18]([CH3:38])[CH:17]=1.CN(C)C=O>C(#N)C.C(OCC)C.C(O)C>[CH3:38][C:18]1[CH:17]=[C:16]([NH:15][C:12]([NH:13][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[S:11])[CH:37]=[CH:36][C:19]=1[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:29])[CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 7679Phenylacetyl chlorideHCID 516872Potassium thiocyanateHCID 57677565Morpholine-4-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide

Produkt 1

HCID 57677541Morpholine-4-carboxylic acid {4-[2-methyl-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-phenylacetyl chloride (0.0523 ml) in acetonitrile (5.0 ml) was added potassium thiocyanate (35.6 mg), followed by stirring under a nitrogen atmosphere at 50° C. for 1 hr. The reaction mixture was cooled down to room temperature, and then morpholine-4-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridine-2-yl]amide (80 mg) and N,N-dimethylformamide (1 ml) were added thereto, followed by stirring under a nitrogen atmosphere at room temperature for 21 hrs. The reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a solid, which was suspended in diethyl ether (4 ml)-ethanol (0.8 ml). The solid was filtered off, washed with diethyl ether, and dried under aeration to provide the titled compound (38 mg, 31%) as colorless powder.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringby stirring under a nitrogen atmosphere at room temperature for 21 hrs
  3. customThe reaction mixture was partitioned between ethyl acetate (100 ml) and water (40 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent; ethyl acetate)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated
  11. customto give a solid, which
  12. filtrationThe solid was filtered off
  13. washwashed with diethyl ether
  14. customdried under aeration

Quellen und Nachweise

ORD-Eintrag
ord-b2dcf3806dde4311904453cc29d95adc
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07531532B2

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