Trifluoroacetic 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-alaninate trifluoroacetate

HRID 1968338Notes

Reaction equation

HRID 1968338 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]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[N:26]=[C:25]([S:36][CH2:37][C:38]3[N:39]=[C:40]([C:43]4[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=4)[S:41][CH:42]=3)[C:24]=2[C:50]#[N:51])=[CH:19][CH:18]=1)=[O:12])[CH3:10])=O)(C)(C)C.[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55]>ClCCl>[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55].[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]([N:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[N:26]=[C:25]([S:36][CH2:37][C:38]3[N:39]=[C:40]([C:43]4[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=4)[S:41][CH:42]=3)[C:24]=2[C:50]#[N:51])=[CH:19][CH:18]=1)=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 687678072-{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-alaninate

Product 1

HCID 687647022-{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-alaninate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg (0.335 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-alaninate (Example 25A) were initially charged in 3.5 ml of dichloromethane. 0.258 ml (3.354 mmol) of trifluoroacetic acid was added, and the reaction solution was then stirred at RT overnight. After one day, another 0.125 ml (1.624 mmol) of trifluoroacetic acid was added to the reaction. The reaction solution was concentrated by evaporation and the residue was triturated with diethyl ether. The solid formed was filtered off. This gave 255 mg (98% of theory) of the target compound.

Workup

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

Sources & evidence

ORD record
ord-99db9cf954514757a379b5f52428ed38
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

Loading…