7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine → 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine

HRID 81985

Reaktionsgleichung

Reaktionsgleichung von HRID 81985
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:12]([N+:17]([O-])=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:28][CH3:29])=[C:5]([CH3:30])[O:4][N:3]=1>C(OCC)(=O)C.CO.[Pd].O.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:28][CH3:29])=[C:5]([CH3:30])[O:4][N:3]=1

Komponenten

7

Edukt 1

HCID 709799137-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine

Produkt 1

HCID 709811557-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamineAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 23938PalladiumLösungsmittelHCID 493570RiboflavinLösungsmittel

Versuchsvorschrift

7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine (for a preparation see Intermediate 16) (1.2 g, 2.91 mmol) was dissolved in a mixture of ethyl acetate (60 ml) and methanol (10 ml) and hydrogenated over Pd/C (0.310 g, 2.91 mmol, 5% w/w, 50% water, Type E101 NO/W) for 24 h at atmospheric pressure under a hydrogen burette. The mixture was filtered and evaporated and the residue was dissolved in DCM (3 ml) and loaded onto a 50 g silica column, then eluted with 0-15% 2M methanolic ammonia/DCM and product containing fractions evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine (0.45 g, 1.177 mmol, 40.4% yield) as a pale yellow solid. LCMS (formate) Rt 0.68 min, MH+ 384

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. dissolutionthe residue was dissolved in DCM (3 ml)
  4. washeluted with 0-15% 2M methanolic ammonia/DCM and product
  5. additioncontaining fractions
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7bf2d387fa814925847b8c8beedd5ba0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846709B2

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