2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile → 6-(3-aminophenyl)-2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17281

Reaktionsgleichung

Reaktionsgleichung von HRID 17281
[C:1]([C:5]1[O:6][C:7]2[C:8](=[C:10]([C:32]#[N:33])[C:11]([CH3:31])=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)[C:13]=2[N:14]2[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>Cl>[NH2:28][C:24]1[CH:23]=[C:22]([C:12]2[C:13]([N:14]3[CH2:18][CH2:17][C@H:16]([N:19]([CH3:20])[CH3:21])[CH2:15]3)=[C:7]3[O:6][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[N:9][C:8]3=[C:10]([C:32]#[N:33])[C:11]=2[CH3:31])[CH:27]=[CH:26][CH:25]=1

Komponenten

3

Edukt 1

HCID 685844192-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685852886-(3-aminophenyl)-2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrileAusbeute 17,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile (I-22) (30.7 mg, 68.6 μmol) was dissolved in 4 N hydrogen chloride (ethyl acetate solution, 2 ml) and the solvent was concentrated under reduced pressure. The residue was dissolved in methanol (8 ml), followed by catalytic hydrogenation at room temperature under normal pressure for 3 hours in the presence of 5% palladium-carbon (50% wet, 30 mg). The catalyst was separated by filtration, the filtrate was concentrated under reduced pressure, aqueous 10% sodium carbonate solution and ethyl acetate were added to the residue followed by stirring. The organic layer was collected by liquid-liquid separation, concentrated and purified by preparative TLC (developing solvent, chloroform:methanol=10:1) to obtain the entitled compound (4.9 mg) as a brown solid.

Aufarbeitung

  1. concentrationthe solvent was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (8 ml)
  3. customThe catalyst was separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure, aqueous 10% sodium carbonate solution and ethyl acetate
  5. additionwere added to the residue
  6. customThe organic layer was collected by liquid-liquid separation
  7. concentrationconcentrated
  8. custompurified by preparative TLC (developing solvent, chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-86a44a0b379545d8b8b65129dc61708d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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