Methyl(4-aminophenoxy)acetate → methyl 2-[4-[[2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]amino]phenoxy]acetate

HRID 1508679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508679
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.Cl.Cl[C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[N:19]=[C:18]2[CH2:29][CH2:30][CH2:31][C:17]=12>CO.ClCCl>[Cl:28][C:24]1[CH:23]=[C:22]([C:20]2[N:19]=[C:18]3[CH2:29][CH2:30][CH2:31][C:17]3=[C:16]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=3)[CH:21]=2)[CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 2

HCID 6422115Methyl(4-aminophenoxy)acetateHCID 901118224-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine HCl salt

Produkt 1

HCID 90112439methyl 2-[4-[[2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]amino]phenoxy]acetateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

An 18-mL vial was charged with methyl 2-(4-aminophenoxy)acetate (24 mg, 0.13 mmol, 2 eq.) and 4-Chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine HCl salt (20 mg, 0.066 mmol, 1 eq. See step 1 of EXAMPLE 1). The mixture was dissolved in a mixture of MeOH (1 ml) and dichloromethane (2 ml). After the volatile material was removed under reduced pressure, the residue was heated at 150° C. under argon for 1 hr. After cooling to room temperature, the reaction mixture was partitioned between NaHCO3 aq. (10 ml) and ethyl acetate (10 ml). The organics was separated and dried over MgSO4. The solvent was removed under reduced pressure to give a residue, which was purified by chromatography on silica gel using dichloromethane followed by 0.1˜0.3% methanol in dichloromethane as eluent to give the desired product methyl 2-[4-[[2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]amino]phenoxy]acetate as white solid (11.8 mg, 44% yield).

Aufarbeitung

  1. customAfter the volatile material was removed under reduced pressure
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was partitioned between NaHCO3 aq. (10 ml) and ethyl acetate (10 ml)
  4. customThe organics was separated
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customto give a residue, which
  8. customwas purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bdb336c843634f49a2e9bda1856c05db
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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