Tetrabutylammonium Fluoride → (5-Amino-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol

HRID 2167640노트

반응식

HRID 2167640 반응식
[Si]([O:8][CH2:9][C:10]1[CH:35]=[CH:34][C:13]2=[C:14]3[C:19](=[C:20]([NH2:22])[N:21]=[C:12]2[CH:11]=1)[N:18]=[CH:17][C:16]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[CH3:33])=[CH:15]3)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:22][C:20]1[C:19]2[N:18]=[CH:17][C:16]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[CH3:33])=[CH:15][C:14]=2[C:13]2[CH:34]=[CH:35][C:10]([CH2:9][OH:8])=[CH:11][C:12]=2[N:21]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 582137038-((Tert-butyldimethylsilyloxy)methyl)-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-5-amine

생성물 1

HCID 58166517(5-Amino-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(Tert-butyldimethylsilyloxy)methyl)-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-5-amine (from step 5) (1.0 equiv.) and TBAF (1.1 equiv.) in THF is stirred at ambient temperature overnight. The reaction is quenched with saturated NaHCO3. The two phases are separated, and the aqueous layer is extracted twice with Et2O. The combined organic layers are washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude material is purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give 5-amino-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol (2-1) as a white solid. 1H NMR (acetone-d6): δ 8.79 (s, 1H), 8.73 (s, 1H), 8.35 (d, 1H), 7.61 (s, 1H), 7.33 (d, 1H), 7.09 (d, 1H), 6.75 (d, 1H), 6.68 (dd, 1H), 6.57 (br s, 2H), 4.47 (d, 2H), 4.32 (t, 1H), 3.58 (s, 3H), 3.17 (t, 2H), 3.04 (t, 2H), 2.30 (s, 3H). LRMS [M+H]=374.2.

후처리

  1. customThe reaction is quenched with saturated NaHCO3
  2. customThe two phases are separated
  3. extractionthe aqueous layer is extracted twice with Et2O
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material is purified by flash chromatography on a COMBIFLASH® system (ISCO)
  8. customto give 5-amino-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol (2-1) as a white solid

출처 및 근거

ORD 기록
ord-2e7f3accbb5c43aa840347574d7dac0b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045470B2

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