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Diisopropylethylamine → HCID 44553916, Verbindung

HRID 2359412
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2359412
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH2:4][O:3]1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:20]=[C:21]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[C:28]([C:35](O)=[O:36])[CH:29]=[CH:30][CH:31]=3)[N:26]=2)[CH:22]=[CH:23][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:35]([C:28]2[CH:29]=[CH:30][CH:31]=[C:32]3[C:27]=2[N:26]=[C:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:39])([F:17])[F:38])[CH:20]=2)[CH:34]=[CH:33]3)=[O:36])=[CH:14][CH:15]=1
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Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575815714-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)anilineHCID 58154625HCID 58154625, Verbindung

Produkt 1

HCID 44553916HCID 44553916, Verbindung
Ausbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a mixture of 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline (167 mg, 0.750 mmol), 2-(3-(trifluoromethyl)phenyl)quinoline-8-carboxylic acid (159 mg, 0.500 mmol), HATU (285 mg, 0.75 mmol) in NMP (5 mL) was added DIPEA (173 μL, 1.0 mmol). The reaction was stirred for 72 hours at room temperature, water (5 mL) was added and the resulting precipitates were collected by filtration and recrystallized from ethanol. The yellow solid was treated with a mixture of 1:3 6N HCl/Dioxane (8 mL) overnight. The mixture was concentrated to dryness, triturated with water, collected by filtration, washed with water and dried to obtain N-(4-(2,3-dihydroxypropoxy)phenyl)-2-(3-(trifluoromethyl)phenyl)quinoline-8-carboxamide (191 mg, 79% yield). MS (ESI) calcd for C26H21F3N2O4 (m/z): 482.15. found: 483 [M+1].

Aufarbeitung

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethanol
  4. additionThe yellow solid was treated with a mixture of 1:3 6N HCl/Dioxane (8 mL) overnight
  5. concentrationThe mixture was concentrated to dryness
  6. customtriturated with water
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ccd84f44314d48aeb98ad1fbbc66aab5
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685970B2

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