Tetrabutylammonium Fluoride → HCID 58213665, compound

HRID 340359Notes

Reaction equation

HRID 340359 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:35]=[CH:34][C:15]([CH2:16][CH2:17][C:18]2[CH:19]=[N:20][C:21]3[C:26]([CH:27]=2)=[C:25]2[CH:28]=[CH:29][C:30]([CH3:32])=[CH:31][C:24]2=[N:23][C:22]=3[NH2:33])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C.O>[NH2:33][C:22]1[C:21]2[N:20]=[CH:19][C:18]([CH2:17][CH2:16][C:15]3[CH:34]=[CH:35][C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:13][CH:14]=3)=[CH:27][C:26]=2[C:25]2[CH:28]=[CH:29][C:30]([CH3:32])=[CH:31][C:24]=2[N:23]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58213754HCID 58213754, compound

Product 1

HCID 58213665HCID 58213665, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)phenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (from the previous step) (1.0 equiv.) in tetrahydrofuran (0.10 M) was added a 1.0 M solution of tetrabutylammonium fluoride (5 equiv.) in THF and the resulting mixture was allowed to stir at 22° C. for 2 hours. At this point, the mixture was diluted with ethyl acetate and water. The biphasic layers were separated and the aqueous layer was washed twice with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-10% methanol in dichloromethane to furnish 2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenoxy)ethanol as a solid. 1H NMR (Acetone-d6): δ 8.76 (s, 1H), 8.67 (s, 1H), 8.28 (d, 1H), 7.40 (s, 1H), 7.15 (t, 3H), 6.84 (d, 2H), 6.54 (br, 2H), 4.00 (t, 2H), 3.83 (t, 2H), 3.21 (t, 2H), 3.05 (t, 2H), 2.45 (s, 3H). LRMS [M+H]=374.2

Workup

  1. customThe biphasic layers were separated
  2. washthe aqueous layer was washed twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customthe volatiles were removed in vacuo
  5. customThe resulting residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-539dff998a1a4ab482426b75e501945e
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

Loading…