Triethylamine → HCID 86711679, Verbindung

HRID 710655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710655
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[I:17][C:18]1[CH:19]=[N:20][N:21]([CH2:23][C:24](O)=[O:25])[CH:22]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:24](=[O:25])[CH2:23][N:21]4[CH:22]=[C:18]([I:17])[CH:19]=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 195766471H-pyrazole-1-acetic acid, 4-iodo-HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Produkt 1

HCID 86711679HCID 86711679, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.400 g, 1.83 mmol), 2-(4-iodo-pyrazol-1-yl)acetic acid (0.554 g, 2.2 mmol) and NEt3 (0.642 mL, 4.59 mmol) in DMF (5 mL) was added HATU (0.836 g, 2.2 mmol). The mixture was stirred at rt for 40 min. It was then quenched with water. The mixture was partitioned between EtOAc (100 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (SiO2, with a gradient elution of 0˜30% EtOAc/CH2Cl2) to yield 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-(4-iodopyrazol-1-yl)ethanone (0.82 g, 100%).

Aufarbeitung

  1. customIt was then quenched with water
  2. customThe mixture was partitioned between EtOAc (100 mL) and sat. NaHCO3 (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2
  7. washwith a gradient elution of 0˜30% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9c62d5aeb1a743e684952479da46c1d4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181241B2

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