Tetrabutylammonium Fluoride → HCID 10201240, compound

HRID 719198Notes

Reaction equation

HRID 719198 reaction equation
[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH2:27][CH2:28][OH:29])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 11060371HCID 11060371, compound

Product 1

HCID 10201240HCID 10201240, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (125 mg) in tetrahydrofuran (5 mL) was added a 1.0M solution of tetrabutyl ammonium fluoride (1.2 mL). After stirring for 1.5 hours the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield crude product which was purified using flash chromatography to yield the title compound as an orange solid (24 mg).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield crude product which
  5. customwas purified

Sources & evidence

ORD record
ord-f1408d0223ac466093294e35f404adaf
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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