Acetyl chloride → N-(5-(4-Acetyl-1-piperazinyl)-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 79128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79128
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:28]=[CH:29][N:30]=[CH:31][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[C:41](Cl)(=[O:43])[CH3:42]>CN(C=O)C>[C:41]([N:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[C:8]5[CH:28]=[CH:29][N:30]=[CH:31][C:7]=5[N:6]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)[C:10]=4[N:11]=3)=[N:17][CH:18]=2)[CH2:23][CH2:24]1)(=[O:43])[CH3:42]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 441325859-Cyclopentyl-N-(5-Piperazin-1-Ylpyridin-2-Yl)pyrido[4,5]pyrrolo[1,2-D]pyrimidin-2-Amine

Produkt 1

HCID 58300101N-(5-(4-Acetyl-1-piperazinyl)-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amineAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of compound 7 (207 mg, 0.50 mmol) in DMF (5 mL) were added N,N-diisopropylethylamine (174 uL, 1.0 mmol) and acetyl chloride (43 uL, 0.60 mmol) in DMF (2 mL) at 0° C. and the resulted mixture was stirred at 0° C. for 1 hr. The reaction mixture was concentrated and the residue was washed with water (sonicated) and the solid was collected by filtration, dried under high vacuumn to give compound 186 (170 mg, 74% yield) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 9.82 (1H, s), 9.27 (1H, s), 9.01 (1H, s), 8.44 (1 H, d, J=5 Hz), 8.21 (1H, d, J=10 Hz), 8.07 (1H, d, J=2 Hz), 8.04 (1H, d, J=5 Hz), 7.52 (1H, dd, J=10 Hz, J=2 Hz), 5.37 (1H, p, J=10 Hz), 3.61 (4H, q, J=5 Hz), 3.17 (2H, t, J=5 Hz), 3.10 (2H, t, J=5 Hz), (3H, s), 2.40 (2H, m), 2.08 (4H, m), 2.06 (3H, s), 1.78 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 456.1, Calculated 456.2.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with water (sonicated)
  3. filtrationthe solid was collected by filtration
  4. customdried under high vacuumn

Quellen und Nachweise

ORD-Eintrag
ord-495027a01c1a40958e7720e2dcdf2e16
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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