Trifluoroacetic acid → N-[2-(3-Aminopropylsulfanyl)-1-(3-methylbut-2-enyl)-1H-benzimidazol-6-yl]benzamide trifluoroacetic acid salt

HRID 1714181Notes

Reaction equation

HRID 1714181 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([S:18][CH2:19][CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)[N:15]([CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[C:14]=2[CH:35]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>O>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[NH2:22][CH2:21][CH2:20][CH2:19][S:18][C:16]1[N:15]([CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[C:14]2[CH:35]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59464724tert-Butyl {3-[6-benzoylamino-1-(3-methylbut-2-enyl)-1H-benzimidazol-2-ylsulfanyl]propyl}carbamate

Product 1

HCID 16042848N-[2-(3-Aminopropylsulfanyl)-1-(3-methylbut-2-enyl)-1H-benzimidazol-6-yl]benzamide trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

33 mg (0.07 mmol) of tert-butyl {3-[6-benzoylamino-1-(3-methylbut-2-enyl)-1H-benzimidazol-2-ylsulfanyl]propyl}carbamate were dissolved in 102 μl of trifluoroacetic acid and 100 μl of water and stirred at room temperature for 6 hours. The reaction mixture was diluted with water and freeze-dried. 34 mg of the desired product were obtained in quantitative yield.

Workup

  1. customfreeze-dried

Sources & evidence

ORD record
ord-d4762a5c908e403abbc07e61b38d823e
Source dataset
uspto-grants-2010_09
Patent number
US07795445B2

Reaction notes

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