Tetrabutylammonium Fluoride → HCID 18378600, compound

HRID 2298809Notes

Reaction equation

HRID 2298809 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([C:30]([N:32]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])[CH:27]=[CH:26][C:4]=1[C:5]([NH:7][C:8]1[C:16]2[N:15]=[C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([C:30]([N:32]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])[CH:27]=[CH:26][C:4]=1[C:5]([NH:7][C:8]1[C:16]2[N:15]=[C:14]([CH2:17][OH:18])[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69962333HCID 69962333, compound

Product 1

HCID 18378600HCID 18378600, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-N-(2-tert-butyldimethylsiloxymethyl-1H-benzimidazol-4-yl)-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzamide (250 mg) and tetrabutylammonium fluoride (1 mol solution in tetrahydrofuran 0.9 ml) in tetrahydrofuran (15 ml) was stirred at room temperature for 4 hours, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography (1% methanol in chloroform) to give 2-methoxy-N-(2-hydroxymethyl-1H-benzimidazol-4-yl)-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzamide (125 mg).

Workup

  1. customthe solvent was removed by evaporation
  2. customThe residue was purified by silica gel column chromatography (1% methanol in chloroform)

Sources & evidence

ORD record
ord-d7df418f3b2b4d6894706079483f9024
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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