Triethylamine → N-[6-(Pyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 2041930

Reaktionsgleichung

Reaktionsgleichung von HRID 2041930
C(P(=O)(OCC)OCC)#N.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[C:16]([C:29](O)=[O:30])=[CH:15]2.[NH2:32][C:33]1[CH:34]=[N:35][C:36]([N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:37][CH:38]=1.C(N(CC)CC)C>CN(C)C=O>[N:39]1([C:36]2[N:35]=[CH:34][C:33]([NH:32][C:29]([C:16]3[N:17]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[C:18]4[C:14]([CH:15]=3)=[CH:13][C:12]([F:11])=[CH:20][CH:19]=4)=[O:30])=[CH:38][CH:37]=2)[CH2:43][CH2:42][CH2:41][CH2:40]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 38991726-(Pyrrolidin-1-yl)pyridin-3-amineHCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

Produkt 1

HCID 23728638N-[6-(Pyrrolidin-1-yl)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.28 ml (1.68 mmol) of diethyl cyanophosphonate is added, dropwise, at 20° C. under argon, to a solution of 0.402 g (1.4 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid (example 1.1) and of 0.274 g (1.68 mmol) of 3-amino-6-(pyrrolidin-1-yl)pyridine (WO 02/48152) in 10 ml of dry dimethylformamide. The mixture is stirred for ten minutes and then 0.43 ml (3.08 mmol) of triethylamine is added dropwise. The mixture is stirred at ambient temperature for 18 hours, concentrated under reduced pressure, and then taken up with 50 ml of ethyl acetate. This solution is then successfully washed with three times 20 ml of a saturated sodium hydrogen carbonate solution, 50 ml of water and 20 ml of a saturated sodium chloride solution, and then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The solid obtained is triturated in isopropylether under hot conditions. 0.527 g of a solid is obtained, which solid is dried under reduced pressure.

Aufarbeitung

  1. customat 20° C.
  2. stirringThe mixture is stirred at ambient temperature for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. washThis solution is then successfully washed with three times 20 ml of a saturated sodium hydrogen carbonate solution, 50 ml of water and 20 ml of a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid obtained
  9. customis triturated in isopropylether under hot conditions

Quellen und Nachweise

ORD-Eintrag
ord-e04488103c074ff3940b1da04b0d2961
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586573B2

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