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Hydrochloric Acid → Taprizosin

HRID 1795391
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1795391
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]([O:16][CH3:17])=[C:4]([O:18][CH3:19])[CH:3]=1.[C:20]([N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]1)#[N:21].O.Cl>CS(C)=O.C(OCC)(=O)C>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:18][CH3:19])=[C:5]([O:16][CH3:17])[C:6]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:1]=[C:20]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]2)[N:21]=1
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9856336N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamideHCID 99430356-Amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

Produkt 1

HCID 6433102TaprizosinAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile (see Example 2 or 2A, 7 g, 27 mmol) and N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide (see Example 3 or 3A, 9 g, 36 mmol) in DMSO (21 ml) at room temperature, was added sodium-t-pentoxide (9.5 g, 92 mmol) portionwise over 20 minutes keeping the temperature below 30° C. The resulting slurry was then stirred for 2 hours. After this time, iced water (35 ml) was added over 1 minute followed by ethyl acetate (35 ml) before reducing the pH of the biphasic mixture to 8.0 with 2M aqueous HCl (20 ml). The aqueous phase was extracted with ethyl acetate (50 ml). The combined organics were washed with saturated NaCl solution (2×30 ml), reduced in volume and stirred for 3 hours. After this time, the resulting slurry was filtered to yield 10.2 g (74%) of the title compound.

Aufarbeitung

  1. customthe temperature below 30° C
  2. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  3. washThe combined organics were washed with saturated NaCl solution (2×30 ml)
  4. stirringstirred for 3 hours
  5. filtrationAfter this time, the resulting slurry was filtered

Quellen und Nachweise

ORD-Eintrag
ord-960870f5b2404c689c0b1538900cccde
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07026479B2

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