Tetrabutylammonium Fluoride → HCID 22314103, compound

HRID 270435Notes

Reaction equation

HRID 270435 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH2:36][CH3:37])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:35]=[CH:34][C:18]2[C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[C:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:24][CH:23]=3)=[N:20][S:21][C:17]=2[CH:16]=1)(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:33][N:31]([CH3:32])[CH2:30][C:29]#[C:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[C:18]3[CH:34]=[CH:35][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][N:9]([CH2:36][CH3:37])[CH2:8][CH2:7][OH:6])=[CH:16][C:17]=3[S:21][N:20]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22314082HCID 22314082, compound

Product 1

HCID 22314103HCID 22314103, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

350 mg (0.62 mmol) (3-{4-[6-(4-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-butoxy)-benzo[d]isothiazol-3-yl]-phenyl}-prop-2-ynyl)-dimethyl-amine in 5 ml THF were treated with 0.92 ml 1M Bu4NF in THF at RT for 1 h. The solution was concentrated and the residue was purified by column chromatography on silica gel to give 185 mg (66%) 2-[(4-{3-[4-(3-Dimethylamino-prop-1-ynyl)-phenyl]-benzo[d]isothiazol-6-yloxy}-butyl)-ethyl-amino]-ethanol as light brown oil, MS: 452 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dace78db9c234543ab40c7a09cf03a07
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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