Tetrabutylammonium Fluoride → HCID 58213665, compound

HRID 1259227Notes

Reaction equation

HRID 1259227 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-94d6ee77c9ff45259f5800c2e06ff1b3
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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