Tetrabutylammonium Fluoride → 2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-{[1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]methyl}-N-methylacetamide

HRID 1428412Notes

Reaction equation

HRID 1428412 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][N:21]([CH3:36])[C:22](=[O:35])[CH2:23][N:24]1[C:28]2[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=2[S:26][C:25]1=[O:34])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]2[S:26][C:25](=[O:34])[N:24]([CH2:23][C:22]([N:21]([CH2:20][C:12]3[N:11]([CH2:10][CH2:9][OH:8])[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[N:13]=3)[CH3:36])=[O:35])[C:28]=2[CH:29]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123358874N-{[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-benzimidazol-2-yl]methyl}-2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-methylacetamide

Product 1

HCID 1176524662-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-{[1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]methyl}-N-methylacetamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-{[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-benzimidazol-2-yl]methyl}-2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-methylacetamide (520 mg) and THF (15 mL) was added tetrabutylammonium fluoride (1.0 M THF solution, 1.43 mL), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/MeOH=99/1-90/10). The obtained solid was washed with EtOAc to obtain 2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-{[1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]methyl}-N-methylacetamide (340 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent: chloroform/MeOH=99/1-90/10)
  3. washThe obtained solid was washed with EtOAc

Sources & evidence

ORD record
ord-ed5af7a81aaf416f989da9071889a247
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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