Tetrahydrofuran → N-(3-((5-fluoro-2-((4-hydroxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)-2,3-dihydroxypropanamide

HRID 2274260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2274260
[F:1][C:2]1[C:3]([NH:16][C:17]2[CH:18]=[C:19](NC(=O)C=C)C=C[CH:22]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C[N+:29]1([O-])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[C:36](OCC)(=[O:38])C.C1C[O:45]CC1>O.O=[Os](=O)(=O)=O>[F:1][C:2]1[C:3]([NH:16][C:17]2[CH:22]=[C:34]([NH:29][C:30](=[O:45])[CH:31]([OH:32])[CH2:36][OH:38])[CH:33]=[CH:19][CH:18]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 86724331N-(3-((5-fluoro-2-((4-hydroxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)acrylamide

Produkt 1

HCID 86724334N-(3-((5-fluoro-2-((4-hydroxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)-2,3-dihydroxypropanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 25 mL 3-neck RBF equipped with a calcium chloride guard tube, N-(3-((5-fluoro-2-((4-hydroxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)acrylamide (I-3) (0.100 g), in THF (4 mL), NMO (0.032 g) and OsO4(4% in water) solution were charged at room temperature The reaction mixture was stirred at room temperature for approx. 4 h. The reaction was monitored on TLC using ethyl acetate (100%) as mobile phase. After completion, the reaction mixture was poured in water and extracted into ethyl acetate. Organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure at 40° C. Crude material was purified by preparative HPLC using 0.1% TFA in ACN and 0.1% TFA in water as mobile phase to give 10 mg of N-(3-((5-fluoro-2-((4-hydroxyphenyl)amino)pyrimidin-4-yl)amino)phenyl)-2,3-dihydroxypropanamide. 1H NMR: DMSO-d6 (400 MHz) 3.58-3.61 (m, 2H), 4.045-4.059 (t, 1H, J=4), 4.836-4.851 (d, 1H, J=6), 5.771-5.785 (d, 1H, J=5.6), 6.605-6.627 (d, 2H, J=8.8), 7.201-7.242 (t, 1H, J=8), 7.377-7.442 (m, 3H), 7.541-7.561 (d, 1H, J=8), 7.953 (s, 1H), 8.020-8.029 (d, 1H, J=3.6), 8.827 (s, 1H), 8.931 (s, 1H), 9.300 (s, 1H), 9.520 (s, 1H).

Aufarbeitung

  1. customInto a 25 mL 3-neck RBF equipped with a calcium chloride guard tube
  2. extractionextracted into ethyl acetate
  3. washOrganic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure at 40° C
  6. customCrude material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-82ece546b11a470eac3faae2bb3b7e19
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126950B2

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