Trifluoroacetic acid → HCID 69424678, compound

HRID 1591766Notes

Reaction equation

HRID 1591766 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:12]=[C:13]([S:18](Cl)(=[O:20])=[O:19])[CH:14]=[C:15]([Cl:17])[CH:16]=1.[CH3:22][N:23]([C:44](=[O:49])[CH2:45][CH2:46][NH:47][CH3:48])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33](C(OC(C)(C)C)=O)[CH2:34][CH2:35][N:36]=2)=[CH:28][CH:27]=1.[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>C(#N)C.O>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[Cl:10][C:11]1[CH:12]=[C:13]([S:18]([CH2:48][NH:47][CH2:46][CH2:45][C:44]([N:23]([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]3[NH:36][CH2:35][CH2:34][N:33]=3)=[CH:30][CH:31]=2)[CH3:22])=[O:49])(=[O:20])=[O:19])[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 58638720HCID 58638720, compound

Product 1

HCID 69424678HCID 69424678, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

6.88 μl (65.77 μmol) of diisopropylethylamine and a solution of 3.26 mg (13.15 μmol) of 3,5-dichlorobenzenesulphonyl chloride in 150 μl of acetonitrile were added to a solution of 7.3 mg (13.15 μmol) of tert.-butyl 2-(4-{2-[methyl-(3-methylaminopropionyl)amino]ethyl}phenyl)-4,5-dihydroimidazole-1-carboxylate in 100 μl of acetonitrile. The reaction mixture was stirred at room temperature for 1.5 hours. 500 μl of a solution of trifluoroacetic acid and water (95/5) were then added, and the mixture was stirred at room temperature for a further 30 min. The reaction mixture was then evaporated to dryness in a Christ-Speedvac. The crude product obtained in this manner was purified by HPLC.

Workup

  1. stirringthe mixture was stirred at room temperature for a further 30 min
  2. customThe reaction mixture was then evaporated to dryness in a Christ-Speedvac

Sources & evidence

ORD record
ord-7ad65b91f9064dc186196a345e014eba
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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