Diisopropylethylamine → N-{4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzyl}-3-piperidin-1-yl-propionamide

HRID 133034

Reaktionsgleichung

Reaktionsgleichung von HRID 133034
[N:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.O=C1C=CC=CN1OC(N(C)C)=[N+](C)C.[NH2:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[NH:66][C:52]3[N:53]=[CH:54][N:55]=[C:56]([NH:57][C@@H:58]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)[CH3:59])[C:51]=3[CH:50]=2)=[CH:45][CH:44]=1>CN(C=O)C>[C:60]1([C@H:58]([NH:57][C:56]2[C:51]3[CH:50]=[C:49]([C:46]4[CH:45]=[CH:44][C:43]([CH2:42][NH:41][C:9](=[O:11])[CH2:8][CH2:7][N:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[CH:48][CH:47]=4)[NH:66][C:52]=3[N:53]=[CH:54][N:55]=2)[CH3:59])[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 1177821-Piperidinepropanoic acidHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 59756727[6-(4-Aminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine

Produkt 1

HCID 69180362N-{4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzyl}-3-piperidin-1-yl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

Under an atmosphere of nitrogen a mixture of 0.0865 g (0.55 mmol) 3-piperidin-1-yl-propionic acid and 0.117 ml (0.68 mmol) N,N-diisopropylethylamine in DMF (5 ml) is treated at RT and over a period of 5 min with a solution of 0.163 g (0.56 mmol) O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N′,N′-tetramethyluronium-tetrafluroborate (TPTU, Fluka, Buchs, Switzerland) in 2 ml DMF. After stirring for 5 min the resulting solution is added slowly (1.5. h) at RT to 0.172 g (0.5 mmol) [6-(4-aminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine (step 40.5) in 3 ml DMF. The reaction mixture is allowed to stand over night after which the DMF is evaporated under reduced pressure. The residue is purified by flash chromatography using gradients of first dichloromethane/methanol 100:2.5 to 10:1 and then mixtures of dichloromethane/methanol/conc. ammonia 90:10:0.5 to 40:10:1. The title compound is obtained as yellowish solid; m.p. 140° C.; MS-ES+: (M+H)+=483. As a second product of this reaction N-{4-[4-((R)-1-phenyt-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzyl}-acrylamide is obtained; m.p. 249-250° C.; MS-ES+: (M+H)+=398.

Aufarbeitung

  1. waitto stand over night
  2. customafter which the DMF is evaporated under reduced pressure
  3. customThe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-23b655fbdfc84d17972a51ac5690fecd
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390805B2

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