Dimethylamine → 4-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-N,N,2,2-tetramethylbut-3-ynamide

HRID 333897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333897
[OH:1][C:2]([CH3:34])([CH3:33])[CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([CH3:26])([CH3:25])[C:22](O)=[O:23])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.C[CH2:36][N:37](C(C)C)[CH:38](C)C.N(C)C.C1COCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[OH:1][C:2]([CH3:34])([CH3:33])[CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([CH3:26])([CH3:25])[C:22]([N:37]([CH3:38])[CH3:36])=[O:23])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1

Komponenten

7

Edukt 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 498703204-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-2,2-dimethylbut-3-ynoic acid

Produkt 1

HCID 498703214-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-N,N,2,2-tetramethylbut-3-ynamideAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-2,2-dimethylbut-3-ynoic acid (5.0 mg, 0.011 mmol) and i-Pr2NEt (0.01 mL) in CH2Cl2 (1 mL) were added 2 M Me2NH in THF (0.1 mL, 0.2 mmol) and solid HATU (8.5 mg, 0.022 mmol). The mixture was stirred overnight at rt, concentrated and the residue purified by prep HPLC to afford 4-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-N,N,2,2-tetramethylbut-3-ynamide (1.0 mg, 19%). LC-MS Method 1 tR=1.65 min, m/z=491, 433; 1H NMR (CDCl3) 1.13 (s, 3H), 1.18 (s, 3H), 1.52 (d, 3H), 1.55 (s, 6H), 2.10-2.40 (5H), 2.82 (m, 1H), 5.64 (q, 1H), 6.88 (d, 2H), 7.13 (d, 2H), 7.30-7.40 (5H)

Aufarbeitung

  1. concentrationconcentrated
  2. customthe residue purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5ef0046bdc174ca7804078ec974b2672
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883778B2

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