Triethylamine → 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide

HRID 29884

Reaktionsgleichung

Reaktionsgleichung von HRID 29884
Cl.[F:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[O:16])[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.Cl[C:26]1[C:27]2[C:34]([CH3:35])=[CH:33][NH:32][C:28]=2[N:29]=[CH:30][N:31]=1.C(N(CC)CC)C>C(O)(C)C>[F:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]([CH:17]3[CH2:18][CH2:19][N:20]([C:26]4[C:27]5[C:34]([CH3:35])=[CH:33][NH:32][C:28]=5[N:29]=[CH:30][N:31]=4)[CH2:21][CH2:22]3)=[O:16])[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 86607288Piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide hydrochloride

Produkt 1

HCID 117192531-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

A mixture of piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide hydrochloride (2.51 g, 7.16 mmol) and 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 5.97 mmol) in iso-propanol (15 mL) was placed in a microwave vessel, followed by addition of triethylamine (2.5 mL, 18 mmol). The microwave vessel was sealed then heated in the microwave at normal absorbance at 190° C. for 60 min. The mixture was concentrated to remove most of the iso-propanol and triethylamine. The residue was washed with methanol (2×15 mL) to afford a brown solid. The solid was washed with water (3×30 mL) and dried overnight to afford 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid [3-(4-fluoro-phenoxy)-phenyl]-amide (1.83 g, 69%) as a light-brown solid ((M+H)+: 446.3).

Aufarbeitung

  1. customwas placed in a microwave vessel
  2. customThe microwave vessel was sealed
  3. concentrationThe mixture was concentrated
  4. customto remove most of the iso-propanol and triethylamine
  5. washThe residue was washed with methanol (2×15 mL)
  6. customto afford a brown solid
  7. washThe solid was washed with water (3×30 mL)
  8. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-672106cdbdea43eea1976410d4c21625
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423043B2

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