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Hydrochloric Acid → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-isoleucyl-L-alaninate hydrochloride

HRID 1968348
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1968348
C(OC([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:19]([O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:36]([C:37]#[N:38])=[C:35]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[N:34]=[C:33]([S:44][CH2:45][C:46]3[N:47]=[C:48]([C:51]4[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=4)[S:49][CH:50]=3)[C:32]=2[C:58]#[N:59])=[CH:27][CH:26]=1)=[O:20])[CH3:18])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=O)(C)(C)C.Cl>ClCCl.C(OCC)C>[ClH:57].[NH2:8][C@H:9]([C:14]([NH:16][C@H:17]([C:19]([O:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[C:36]([C:37]#[N:38])=[C:35]([N:39]3[CH2:40][CH2:41][CH2:42][CH2:43]3)[N:34]=[C:33]([S:44][CH2:45][C:46]3[N:47]=[C:48]([C:51]4[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=4)[S:49][CH:50]=3)[C:32]=2[C:58]#[N:59])=[CH:29][CH:30]=1)=[O:20])[CH3:18])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11]
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Komponenten

5

Edukt 2

HCID 313Hydrochloric Acid2×HCID 687635572-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-isoleucyl-L-alaninate

Produkt 1

HCID 687639812-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-isoleucyl-L-alaninate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

414 mg (0.482 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-isoleucyl-L-alaninate were dissolved in 3 ml dichloromethane, and 4.822 ml of a 1N solution of hydrogen chloride in diethyl ether were added. After 6 hours of stirring, 2 ml of a 1N solution of hydrogen chloride in diethyl ether were added, and the mixture was stirred at room temperature for a further 24 hours. The precipitated solid was filtered off with suction, washed with diethyl ether and dried under reduced pressure. Since the reaction was still incomplete, the solid was stirred in 5 ml of a 1N solution of hydrogen chloride in diethyl ether for a further 24 h. The precipitated solid was filtered off with suction, washed with diethyl ether and dried under reduced pressure. 312 mg (81% of theory) of the target compound were obtained.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for a further 24 hours
  2. filtrationThe precipitated solid was filtered off with suction
  3. washwashed with diethyl ether
  4. customdried under reduced pressure
  5. stirringthe solid was stirred in 5 ml of a 1N solution of hydrogen chloride in diethyl ether for a further 24 h
  6. filtrationThe precipitated solid was filtered off with suction
  7. washwashed with diethyl ether
  8. customdried under reduced pressure
  9. custom312 mg (81% of theory) of the target compound were obtained

Quellen und Nachweise

ORD-Eintrag
ord-c801c6e4c085440db9d91c12fc078442
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08420825B2

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