Hydrochloric Acid → 6-Acetyl-8-cyclopentyl-5-methyl-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-8H-pyrido(2,3-d)pyrimidin-7-one

HRID 1271976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271976
C(O[C:6](=O)[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]3[N:21]=[CH:22][C:23]4[C:29]([CH3:30])=[C:28]([C:31]([O:33]CC)=[CH2:32])[C:27](=[O:36])[N:26]([CH:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[C:24]=4[N:25]=3)=[CH:17][CH:18]=2)[CH2:9]1)(C)(C)C.Cl>C(Cl)(Cl)Cl>[C:31]([C:28]1[C:27](=[O:36])[N:26]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:24]2[N:25]=[C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:13]([N:10]4[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]4)=[CH:14][N:15]=3)[N:21]=[CH:22][C:23]=2[C:29]=1[CH3:30])(=[O:33])[CH3:32]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 10196694(1-{6-[8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 53302986-Acetyl-8-cyclopentyl-5-methyl-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-8H-pyrido(2,3-d)pyrimidin-7-oneAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of (1-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (394 mg, 0.68 mmol) in chloroform (5 ml) was added hydrogen chloride (2 M ethereal solution, 2.0 ml, 4.0 mmol). The reaction mixture was stirred at RT for 12 h. The solvents were evaporated and the residue was dissolved in ethanol. The ethanol was evaporated to give 6-acetyl-8-cyclopentyl-5-methyl-2-[5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamino]-8H-pyrido[2,3-d]pyrimidin-7-one (239 mg, 0.52 mmol). MS (APCI+) 487, 391, 279 (100); 1H NMR δ (400 MHz, DMSOd6) 8.98 (s, 1H), 8.34 (br, 2H), 7.78–7.73 (m, 2H), 7.51 (br, 1H), 5.89–5.80 (m, 1H), 3.98 (br, 2H), 3.62–3.51 (m, 4H), 2.40–3.23 (m, 2H), 2.44 (s, 3H), 2.25–2.20 (m, 2H), 2.16–2.13 (m, 1H), 1.93 (br, 2H), 1.80–1.78 (m, 2H), 1.61–1.58 (m, 2H); Anal. Calc'd for C24H29N7O2, 2.10 HCl, 2.85 H2O, 0.45 C2H5OH: C, 50.16; H, 6.68; N, 16.45; Cl−, 12.49. Found: C, 50.37; H, 6.90; N, 16.45; Cl−, 12.61.

Aufarbeitung

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in ethanol
  3. customThe ethanol was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-02f5a8bcbb7540e888ef241691b6b7a2
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208489B2

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