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-alaninate trifluoroacetate

HRID 1621342Notes

Reaction equation

HRID 1621342 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]([S:31][CH2:32][C:33]3[N:34]=[C:35]([C:38]4[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=4)[S:36][CH:37]=3)[N:26]=[C:25]([N:45]3[CH2:48][CH2:47][CH2:46]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]([S:31][CH2:32][C:33]3[N:34]=[C:35]([C:38]4[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=4)[S:36][CH:37]=3)[N:26]=[C:25]([N:45]3[CH2:46][CH2:47][CH2:48]3)[C:24]=2[C:49]#[N:50])=[CH:19][CH:18]=1)=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687632332-{4-(2-(Azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate

Product 1

HCID 687629082-{4-(2-(azetidin-1-yl)-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyanopyridin-4-yl)phenoxy}ethyl L-alaninate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

39 mg (0.053 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 N-(tert-butoxycarbonyl)-L-alaninate (Example 13A) were initially charged in 1.5 ml dichloromethane. 0.5 ml (6.49 mmol) of trifluoroacetic acid was added, and the reaction solution was then stirred at RT for 1.5 h. The reaction solution was concentrated by evaporation and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 40 mg (100% 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-c83b7adf95b443a2a0acf068c218e61b
Source dataset
uspto-grants-2014_07
Patent number
US08772498B2

Reaction notes

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