Hydrochloric Acid → HCID 90293527, Verbindung

HRID 1631040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631040
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([OH:9])=[O:8].[CH3:10]OC(OC)(C)C.Cl.[Cl:18][C:19]1[C:20](Cl)=[N:21][CH:22]=[C:23]([CH:26]=1)[C:24]#[N:25].CCN(C(C)C)C(C)C>CO.CC#N.C(Cl)Cl>[Cl:18][C:19]1[C:20]([NH:1][C@H:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[C:7]([O:9][CH3:10])=[O:8])=[N:21][CH:22]=[C:23]([C:24]#[N:25])[CH:26]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 73305CispentacinHCID 81531DiisopropylethylamineHCID 128784645,6-Dichloropyridine-3-carbonitrile

Produkt 1

HCID 90293527HCID 90293527, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of cis-2-amino-1-cyclopentanecarboxylic acid (0.403 g; 3.12 mmol) and 2,2-dimethoxypropane (3 mL) in MeOH (5 mL) was treated with concentrated hydrochloric acid (2 mL). The reaction mixture was heated under reflux for 8 hours. The solvent was evaporated in vacuo. The residue was combined with 5,6-dichloronicotinonitrile (Bionet, 0.346 g; 2.00 mmol), DIEA (0.348 mL; 2.00 mmol) in MeCN (10 mL). The reaction mixture was heated under reflux for 24 hours. The reaction mixture was diluted with DCM and washed with water. The organic phase was passed through a hydrophobic frit and the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (60 iso-hexane to 10 EtOAc) to afford the title product. 1H NMR (CDCl3, 400 MHz) δ 8.29 (1H, d, J=2 Hz), 7.61 (1H, d, J=2 Hz), 6.29 (1H, br d, J=7.6 Hz), 4.76-4.68 (1H, m), 3.63 (3H, s), 3.16-3.10 (1H, m), 2.16-1.78 (6H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customThe solvent was evaporated in vacuo
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 24 hours
  6. washwashed with water
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica
  9. washeluting with iso-hexane/EtOAc (60 iso-hexane to 10 EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-da6dac7911634a7fbb6210bcc33a66b0
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791142B2

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