Hydrochloric Acid → 3-amino-6-(4-{3-[(3-methoxypropyl)amino]propyl}phenyl)-N-pyridin-3-ylpyrazine-2-carboxamide

HRID 217778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217778
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][N:26]([CH2:34][CH2:35][CH2:36][O:37][CH3:38])C(=O)OC(C)(C)C)=[CH:19][CH:18]=2)=[N:6][C:7]=1[C:8](=[O:16])[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.Cl.[OH-].[Na+]>CCOC(C)=O.O>[NH2:1][C:2]1[C:7]([C:8]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:16])=[N:6][C:5]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][NH:26][CH2:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:21][CH:22]=2)=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66678170Tert-butyl (3-{4-[5-amino-6-(pyridin-3-ylcarbamoyl)pyrazin-2-yl]phenyl}propyl)(3-methoxypropyl)carbamate

Produkt 1

HCID 533023753-amino-6-(4-{3-[(3-methoxypropyl)amino]propyl}phenyl)-N-pyridin-3-ylpyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the product of step (v) (300 g, 0.58 mol) in 4N—HCl in EtOAc (3 L) was stirred for 3 hours. The suspension was filtered and the yellow solid obtained. The solid was dissolved in H2O (1.2 L). 2N—NaOH was added dropwise into the solution to basified to pH=11. The mixture was extracted with a mixture of THF and EtOAc (5 L×2, 1:1) and the organic phase washed with aqueous 10%—NaCl and concentrated in vacuo. The subtitle compound (vi) was obtained (pale yellow solid, 210 g).

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. customthe yellow solid obtained
  3. extractionThe mixture was extracted with a mixture of THF and EtOAc (5 L×2, 1:1)
  4. washthe organic phase washed with aqueous 10%—NaCl
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3034a541a6194adcba2ea74e4c39f84d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198285B2

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