Trifluoroacetic acid → 2-{4-(2-(Azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl L-lysyl-L-alaninate bis(trifluoroacetate)

HRID 1968344Notes

Reaction equation

HRID 1968344 reaction equation
C(OC([NH:8][C@H:9]([C:22]([NH:24][C@H:25]([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]([S:47][CH2:48][C:49]3[N:50]=[C:51]([C:54]4[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=4)[S:52][CH:53]=3)[N:42]=[C:41]([N:61]3[CH2:64][CH2:63][CH2:62]3)[C:40]=2[C:65]#[N:66])=[CH:35][CH:34]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=O)(C)(C)C.[F:67][C:68]([F:73])([F:72])[C:69]([OH:71])=[O:70]>ClCCl>[F:67][C:68]([F:73])([F:72])[C:69]([OH:71])=[O:70].[F:67][C:68]([F:73])([F:72])[C:69]([OH:71])=[O:70].[NH2:8][C@H:9]([C:22]([NH:24][C@H:25]([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]([S:47][CH2:48][C:49]3[N:50]=[C:51]([C:54]4[CH:55]=[CH:56][C:57]([Cl:60])=[CH:58][CH:59]=4)[S:52][CH:53]=3)[N:42]=[C:41]([N:61]3[CH2:62][CH2:63][CH2:64]3)[C:40]=2[C:65]#[N:66])=[CH:35][CH:34]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866438482-{4-(2-(Azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate

Product 1

HCID 568489822-{4-(2-(Azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl L-lysyl-L-alaninate bis(trifluoroacetate)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

180 mg (0.188 mmol) of 2-{4-(2-(azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate (Example 3A) were initially charged in 5 ml dichloromethane. 1.0 ml (12.98 mmol) of trifluoroacetic acid was added, and the reaction solution was then stirred at RT for 30 min. The reaction solution was concentrated by evaporation and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 153 mg (83% of theory) of the target compound.

Workup

  1. concentrationThe reaction solution was concentrated by evaporation
  2. customthe residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-3c09f7d64fb54de39872268d2a8a720f
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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