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Trifluoroacetic acid → 2-[(4-{3-[(5-Cyanopyridin-2-yl)(heptyl)amino]propyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid trifluoroacetate

HRID 914431
Notes
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Reaction equation

HRID 914431 reaction equation
C([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][CH2:18][NH2:19])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.Cl[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][N:23]=1.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>ClCCl>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[C:26]([C:25]1[CH:28]=[CH:29][C:22]([N:19]([CH2:13][CH2:14][CH2:16][CH2:17][CH2:18][CH2:31][CH3:32])[CH2:18][CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:5])=[O:20])[S:12][CH:13]=2)=[N:23][CH:24]=1)#[N:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 597590072-{[4-(3-Aminopropyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 674010822-[(4-{3-[(5-Cyanopyridin-2-yl)(heptyl)amino]propyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A compound obtained using 2-{[4-(3-aminopropyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester synthesized in Example 33 and 6-chloronicotinonitrile as starting materials and by operations similar to those of Example 265-1 and Example 265-2 was treated with dichloromethane and trifluoroacetic acid, and the mixture was stirred at room temperature for 12 hr. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=50:1) to give the title compound.

Workup

  1. customA compound obtained
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-77926d35954c409bb8de8cd1aa18a51b
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026370B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes