Trifluoroacetic acid → (4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

HRID 1626113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626113
COC1C=CC(C([NH:24][C:25]2[O:26][CH2:27][C@H:28]([F:48])[C@:29]([C:32]3[CH:37]=[C:36]([NH:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[O:45][CH3:46])[CH:35]=[CH:34][C:33]=3[F:47])([CH3:31])[N:30]=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)=CC=1.FC(F)(F)C(O)=O>ClCCl>[F:48][C@H:28]1[CH2:27][O:26][C:25]([NH2:24])=[N:30][C@@:29]1([C:32]1[CH:37]=[C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[O:45][CH3:46])[CH:35]=[CH:34][C:33]=1[F:47])[CH3:31]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71008803[bis-(4-methoxy-phenyl)-phenyl-methyl]-{(4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-amine

Produkt 1

HCID 71008880(4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamineAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of [bis-(4-methoxy-phenyl)-phenyl-methyl]-{(4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-amine (49.8 mg, 76.6 μmol) in dichloromethane (2 ml) was treated at room temperature with trifluoroacetic acid (89.2 mg, 59.9 μl, 766 μmol), and the mixture was stirred for 15 hours. After evaporation at reduced pressure, the dark red residue was purified by chromatography on a silica-NH2 phase using a gradient of heptane/ethyl acetate=100:0 to 50:50 as the eluent. The (4R,5R)-5-fluoro-4-[2-fluoro-5-(2-methoxy-phenylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (22 mg, 82% yield) was obtained as a white foam. MS (ISP): m/z=348.2 [M+H]+.

Aufarbeitung

  1. customAfter evaporation at reduced pressure
  2. customthe dark red residue was purified by chromatography on a silica-NH2 phase

Quellen und Nachweise

ORD-Eintrag
ord-b06a5a8f287c4a909a34d17f0ad89f59
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785436B2

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