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-leucinate trifluoroacetate

HRID 1968313Notes

Reaction equation

HRID 1968313 reaction equation
C(OC([NH:8][C@H:9]([C:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:31]([C:32]#[N:33])=[C:30]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:29]=[C:28]([S:39][CH2:40][C:41]3[N:42]=[C:43]([C:46]4[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=4)[S:44][CH:45]=3)[C:27]=2[C:53]#[N:54])=[CH:22][CH:21]=1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.[F:55][C:56]([F:61])([F:60])[C:57]([OH:59])=[O:58]>ClCCl>[F:55][C:56]([F:61])([F:60])[C:57]([OH:59])=[O:58].[NH2:8][C@H:9]([C:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[C:31]([C:32]#[N:33])=[C:30]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:29]=[C:28]([S:39][CH2:40][C:41]3[N:42]=[C:43]([C:46]4[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=4)[S:44][CH:45]=3)[C:27]=2[C:53]#[N:54])=[CH:24][CH:25]=1)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687646672-{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-leucinate

Product 1

HCID 866438522-{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-leucinate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.37 g (1.74 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-leucinate were initially charged in 15 ml of dichloromethane, and 15.00 ml (194.70 mmol) of trifluoroacetic acid were added. The mixture was stirred at room temperature for 1 h. After removal of the solvent under reduced pressure, the residue was dissolved in 5.00 ml of dichloromethane and 10.00 ml of diethyl ether were added. The residue formed was filtered off with suction. Drying gave 1.09 g (76.1% of theory) of the desired target compound.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. dissolutionthe residue was dissolved in 5.00 ml of dichloromethane
  3. addition10.00 ml of diethyl ether were added
  4. customThe residue formed
  5. filtrationwas filtered off with suction
  6. customDrying
  7. customgave 1.09 g (76.1% of theory) of the desired target compound

Sources & evidence

ORD record
ord-3b553d1f66f24a23a7f8f6da8954f994
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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