Trifluoroacetic acid → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(propyl-amino)pyridin-4-yl)phenoxy}ethyl L-alaninate trifluoroacetate

HRID 1968336Notes

Reaction equation

HRID 1968336 reaction equation
C(OC([NH:8][C@H:9]([C:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[C:27]([NH:31][CH2:32][CH2:33][CH3:34])[N:26]=[C:25]([S:35][CH2:36][C:37]3[N:38]=[C:39]([C:42]4[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=4)[S:40][CH:41]=3)[C:24]=2[C:49]#[N:50])=[CH:19][CH:18]=1)=[O:12])[CH3:10])=O)(C)(C)C.[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54]>ClCCl>[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54].[NH2:8][C@H:9]([C:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[C:27]([NH:31][CH2:32][CH2:33][CH3:34])[N:26]=[C:25]([S:35][CH2:36][C:37]3[N:38]=[C:39]([C:42]4[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=4)[S:40][CH:41]=3)[C:24]=2[C:49]#[N:50])=[CH:19][CH:18]=1)=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687654192-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(propylamino)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate

Product 1

HCID 468509402-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(propyl-amino)pyridin-4-yl)phenoxy}ethyl L-alaninate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

873 mg (1.191 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(propylamino)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate (Example 14A) were initially charged in 29 ml of dichloromethane. 1.84 ml (23.817 mmol) of trifluoroacetic acid were added, and the reaction solution was then stirred at RT overnight. The reaction solution was concentrated by evaporation and the residue was triturated with diethyl ether. The solid formed was filtered off and dried. This gave 914 mg (89% of theory) of the target compound.

Workup

  1. concentrationThe reaction solution was concentrated by evaporation
  2. customthe residue was triturated with diethyl ether
  3. customThe solid formed
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-28a798ea6f3f41559d0a5f85ebd6bc3e
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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