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-lysyl-beta-alaninate dihydrochloride

HRID 1968341Notes

Reaction equation

HRID 1968341 reaction equation
C(OC([NH:8][C@H:9]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:44]([C:45]#[N:46])=[C:43]([N:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)[N:42]=[C:41]([S:52][CH2:53][C:54]3[N:55]=[C:56]([C:59]4[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=4)[S:57][CH:58]=3)[C:40]=2[C:66]#[N:67])=[CH:35][CH:34]=1)=[O:28])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:68]>ClCCl.C(OCC)C>[ClH:65].[ClH:68].[NH2:8][C@H:9]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[C:44]([C:45]#[N:46])=[C:43]([N:47]3[CH2:48][CH2:49][CH2:50][CH2:51]3)[N:42]=[C:41]([S:52][CH2:53][C:54]3[N:55]=[C:56]([C:59]4[CH:60]=[CH:61][C:62]([Cl:65])=[CH:63][CH:64]=4)[S:57][CH:58]=3)[C:40]=2[C:66]#[N:67])=[CH:37][CH:38]=1)=[O:28])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86643854HCID 86643854, compound

Product 1

HCID 687646752-{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-lysyl-beta-alaninate dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

950 mg (0.976 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 N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-beta-alaninate (Example 24A) were initially charged in 25 ml of dichloromethane. 9.76 ml of a 1N solution of hydrogen chloride in diethyl ether were added, and the reaction solution was then stirred at RT overnight. For 15 min, argon was introduced into the reaction mixture, and the mixture was then concentrated by evaporation. This gave 816 mg (99% of theory) of the target compound.

Workup

  1. waitFor 15 min
  2. additionargon was introduced into the reaction mixture
  3. concentrationthe mixture was then concentrated by evaporation

Sources & evidence

ORD record
ord-d70db6da012e40c38d97b597919250ea
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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