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Diisopropylethylamine → methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

HRID 572814
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572814
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[F:8][C:9]1[CH:10]=[C:11]([NH:16][CH:17]([C:19]2[CH:20]=[C:21]([C:34]([O:36][CH3:37])=[O:35])[CH:22]=[C:23]3[C:28]=2[O:27][C:26](S(CC)=O)=[CH:25][C:24]3=[O:33])[CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[F:8][C:9]1[CH:10]=[C:11]([NH:16][CH:17]([C:19]2[CH:20]=[C:21]([C:34]([O:36][CH3:37])=[O:35])[CH:22]=[C:23]3[C:28]=2[O:27][C:26]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])=[CH:25][C:24]3=[O:33])[CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholineHCID 58235048methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylate

Produkt 1

HCID 58235042methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylateAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

(S)-3-methylmorpholine (87 mg, 0.86 mmol) was added to a stirred solution of methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylate (250 mg, 0.57 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.150 mL, 0.86 mmol) in acetonitrile (3 mL) at RT. The resulting brown mixture was stirred at 75° C. for 7 hours. The reaction mixture was concentrated, diluted with DCM, washed with a 1M hydrochloric acid 1M, brine dried over magnesium sulfate and concentrated to afford the crude product which was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM. The solvent was evaporated to dryness to afford methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (90 mg, 34%) as a yellow foam. Spectrum: [M−H]− 457.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with DCM
  3. washwashed with a 1M hydrochloric acid 1M, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM
  8. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6aae7f0fa1e14e96a62d83d88b845e9b
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029374B2

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