Tetrabutylammonium Fluoride → HCID 18355140, compound

HRID 429640Notes

Reaction equation

HRID 429640 reaction equation
[O:1]([CH2:19][C:20]1[NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([NH:31][C:32]3[CH:63]=[CH:62][C:35]([C:36]([N:38]([CH3:61])[C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]=4[O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]([N:54]4[CH2:59][CH2:58][N:57]([CH3:60])[CH2:56][CH2:55]4)=[O:53])=[O:37])=[CH:34][C:33]=3[O:64][CH3:65])=[O:30])[C:22]=2[N:21]=1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:1][CH2:19][C:20]1[NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([NH:31][C:32]3[CH:63]=[CH:62][C:35]([C:36]([N:38]([CH3:61])[C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]=4[O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]([N:54]4[CH2:55][CH2:56][N:57]([CH3:60])[CH2:58][CH2:59]4)=[O:53])=[O:37])=[CH:34][C:33]=3[O:64][CH3:65])=[O:30])[C:22]=2[N:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70104426HCID 70104426, compound

Product 1

HCID 18355140HCID 18355140, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-tert-butyldiphenylsiloxymethyl-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (296 mg) in dry tetrahydrofuran (10 ml) was added tetrabutylammonium fluoride (173 mg) in ice water bath under nitrogen and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in chloroform. The solution was washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1) to give 4-(2-hydroxymethyl-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (200 mg) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-f40a7f4483124d949f0bbc24aa74840c
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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