4-Fluorobenzylamine → HCID 57810203, Verbindung

HRID 455865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455865
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2([C:28]([OH:30])=O)[CH2:27][CH2:26]2)=[O:24])=[CH:18][CH:17]=1.[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([C:25]2([C:28]([NH:37][CH2:36][C:35]3[CH:38]=[CH:39][C:32]([F:31])=[CH:33][CH:34]=3)=[O:30])[CH2:27][CH2:26]2)=[O:24])=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 673264-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57810164849217-77-2

Produkt 1

HCID 57810203HCID 57810203, VerbindungAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 1-[4-(6,7-dimethoxy-quinolin-4-yloxy)-phenylcarbamoyl]-cyclopropanecarboxylic acid (74.3 mg, 0.182 mmol), 4-Fluoro benzylamine (25 μL, 0.219 mmol), DIEA (90.0 μL, 0.544 mmol) in DMA (1.0 mL) was added HATU (203 mg, 0.534 mmol). The resulting solution was stirred at room temperature for 1 hour before adding dropwise to water (10 mL) with stirring. The slurry was sonicated, filtered and the solids were washed with 1N NaOH followed by water. After air drying, the solids were further purified by prep HPLC, affording ′N-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-N′-[(4-fluorophenyl)methyl]cyclopropane-1,1-dicarboxamide (33 mg, 35% yield, 98% pure) as a white solid. 1H NMR (DMSO, d6): 10.82 (s, 1H), 8.80 (d, 1H), 8.50 (t, 1H), 7.83 (d, 2H), 7.74 (s, 1H), 7.56 (s, 1H), 7.30-7.38 (m, 4H), 7.15 (t, 2H), 6.80 (d, 1H), 4.32 (d, 2H), 4.04 (s, 3H), 4.03 (s, 3H), 1.42 (s, 4H).

Aufarbeitung

  1. stirringwith stirring
  2. customThe slurry was sonicated
  3. filtrationfiltered
  4. washthe solids were washed with 1N NaOH
  5. customAfter air drying
  6. customthe solids were further purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a3b3cfd4016d4cdf9f769717ea95a006
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497284B2

Notizen zur Reaktion

Wird geladen…