Morpholine → (3R)-3-(cyclohexylmethyl)-N-{2-[(4-fluorophenyl)amino]ethyl}-4-(morpholin-4-yl)-4-oxobutanamide

HRID 1783860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783860
[CH:1]1([CH2:7][C@H:8]([CH2:12][C:13]([NH:15][CH2:16][CH2:17][NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>ClCCl>[CH:1]1([CH2:7][C@@H:8]([C:9]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:11])[CH2:12][C:13]([NH:15][CH2:16][CH2:17][NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68477765(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid

Produkt 1

HCID 11327594(3R)-3-(cyclohexylmethyl)-N-{2-[(4-fluorophenyl)amino]ethyl}-4-(morpholin-4-yl)-4-oxobutanamideAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid (220 mg, 0.52 mmol) was treated with morpholine (110 μL, 1.26 mmol, 2.4 eq.) and HATU (238 mg, 0.72 mmol, 1.4 eq.). The reagents were dissolved in dry dichloromethane (4 mL) and treated with diisopropylethylamine (315 μL, 1.81 mmol, 3.5 eq.). The reaction was judged to completion by LC/MS, volatiles were evaporated and the reaction was purified by prep-LC/MS and provided 131 mg (0.25 mmol, 40%) of a off-white solid: HPLC-MS calcd. for C23H34FN3O3 (M+H+) 420.3, found 420.5.

Aufarbeitung

  1. customwere evaporated
  2. customthe reaction was purified by prep-LC/MS and

Quellen und Nachweise

ORD-Eintrag
ord-5577055f2f0042359bf67e6684fc6dd9
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501408B2

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