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Sodium Sulfate → ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-5-(1-methyl-piperidin-4-ylamino)-phenyl]-acetate

HRID 1016789
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Reaktionsgleichung

Reaktionsgleichung von HRID 1016789
[O-]S([O-])(=O)=O.[Na+].[Na+].[NH2:8][C:9]1[CH:10]=[C:11]([CH:17]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[C:13]([CH2:15][CH3:16])[CH:14]=1.[CH3:32][N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][CH:17]([C:11]2[CH:10]=[C:9]([NH:8][CH:36]3[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]3)[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:25][CH:26]=1)#[N:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24436Sodium SulfateHCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 86583558ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate

Produkt 1

HCID 86583561ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-5-(1-methyl-piperidin-4-ylamino)-phenyl]-acetateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Na2SO4 (1.09 g, 7.7 mmol) was added to a solution of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (250 mg, 0.77 mmol) obtained in Example 223.4 and 1-methyl-4-piperidone (174 mg, 1.54 mmol) in acetic acid (5 ml) and the mixture was stirred for 15 min. at room temperature. The mixture was subsequently cooled to 0° C. and NaHB(OAc)3 (489 mg, 2.31 mmol) was slowly added portionwise. After 30 min. a saturated solution of NaHCO3 was added and the mixture was extracted with EtOAc. The organic phase was dried and filtered, and the filtrate was concentrated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1). There were obtained 287 mg (89%) of ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-5-(1-methyl-piperidin-4-ylamino)-phenyl]-acetate as a yellowish solid; MS: 421 ([M+H]+).

Aufarbeitung

  1. temperatureThe mixture was subsequently cooled to 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-83334186f7e74a61b802835110dc301a
Quelldatensatz
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06476264B2

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