Morpholine → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-4H-chromen-4-one

HRID 41212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41212
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:25]=[C:26]([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[C:36]2[CH:37]=[C:38]([C:54](O)=[O:55])[CH:39]=[C:40]3[C:45]=2[O:44][C:43]([N:46]2[CH2:51][CH2:50][O:49][C@H:48]([CH3:52])[CH2:47]2)=[CH:42][C:41]3=[O:53])[CH:27]=[C:28]([F:30])[CH:29]=1.CCN(C(C)C)C(C)C.[NH:66]1[CH2:71][CH2:70][O:69][CH2:68][CH2:67]1>CC(N(C)C)=O>[F:30][C:28]1[CH:27]=[C:26]([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[C:36]2[CH:37]=[C:38]([C:54]([N:66]3[CH2:71][CH2:70][O:69][CH2:68][CH2:67]3)=[O:55])[CH:39]=[C:40]3[C:45]=2[O:44][C:43]([N:46]2[CH2:51][CH2:50][O:49][C@H:48]([CH3:52])[CH2:47]2)=[CH:42][C:41]3=[O:53])[CH:25]=[C:24]([F:23])[CH:29]=1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866724358-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid

Produkt 1

HCID 665581388-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-4H-chromen-4-oneAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

TBTU (154 mg, 0.48 mmol) was added to a stirred solution of 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid (90 mg, 0.19 mmol), DIPEA (0.083 mL, 0.48 mmol) dissolved in DMA (2 mL) under nitrogen. The resulting solution was stirred at room temperature for 30 min. Morpholine (0.050 mL, 0.57 mmol) was added and the mixture was stirred at room temperature for 1 h. The reaction mixture was purified by preparative HPLC. The fractions containing the desired compound were evaporated to dryness to afford 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-6-(morpholine-4-carbonyl)-4H-chromen-4-one (68 mg, 66%) as a yellow solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. customThe reaction mixture was purified by preparative HPLC
  3. additionThe fractions containing the desired compound
  4. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b8b71fd715704506924531ca712a58a6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530470B2

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