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Triethylamine → 4-fluoro-2-(4-fluorophenyl)-N-methyl-5-(2-methyl-5-(3-(pyrimidin-2-yl)oxetan-3-ylcarbamoyl)phenyl)benzofuran-3-carboxamide

HRID 1892561
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1892561
[F:1][C:2]1[C:7]2[C:8]([C:18](=[O:21])[NH:19][CH3:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25](O)=[O:26].Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[C:39]1([NH2:43])[CH2:42][O:41][CH2:40]1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:19][CH3:20])=[O:21])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([C:25](=[O:26])[NH:43][C:39]2([C:34]3[N:35]=[CH:36][CH:37]=[CH:38][N:33]=3)[CH2:42][O:41][CH2:40]2)[CH:28]=[CH:29][C:30]=1[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886HexafluorophosphateHCID 592756803-(4-Fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acidHCID 679578123-(Pyrimidin-2-yl)oxetan-3-amine hydrochloride

Produkt 1

HCID 679585654-fluoro-2-(4-fluorophenyl)-N-methyl-5-(2-methyl-5-(3-(pyrimidin-2-yl)oxetan-3-ylcarbamoyl)phenyl)benzofuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a yellow solution mixture of 3-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid (30 mg, 0.071 mmol) and 3-(pyrimidin-2-yl)oxetan-3-amine hydrochloride (16 mg, 0.085 mmol) in DMF (1 ml) in a 25 ml round-bottomed flask was added benzotriazo-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (50 mg, 0.096 mmol), followed by triethylamine (TEA) (0.1 ml, 0.717 mmol), and the reaction mixture stirred for overnight. Ice cooled water was added to the reaction mixture, which was then stirred for 10-15 min. at 0° C. Precipitation was observed. The solid was collected by filtration, washed with cold water, and then dissolved in dichloromethane. The organic was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC. Yield (12 mg, 30%).

Aufarbeitung

  1. additionwas added to the reaction mixture, which
  2. stirringwas then stirred for 10-15 min. at 0° C
  3. customPrecipitation
  4. filtrationThe solid was collected by filtration
  5. washwashed with cold water
  6. dissolutiondissolved in dichloromethane
  7. dry with materialThe organic was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by preparative HPLC
  11. customYield (12 mg, 30%)

Quellen und Nachweise

ORD-Eintrag
ord-3c7f8ccfa2904dbd9722b5bc22a39b5b
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507683B2

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