Triethylamine → 2-(3-Imidazol-1-yl-propylamino)-8-cyclohexyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methoxy-amide

HRID 12365

Reaktionsgleichung

Reaktionsgleichung von HRID 12365
C(N(CC)CC)C.Cl.[CH3:9][O:10][NH2:11].C([O:14][C:15]([C:17]1[C:18](=[O:45])[C:19]2[CH:24]=[N:23][C:22]([NH:25][CH2:26][CH2:27][CH2:28][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[N:21][C:20]=2[N:34]([C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)CCC3)[CH:35]=1)=O)C>CO.O>[CH3:9][O:10][NH:11][C:15]([C:17]1[C:18](=[O:45])[C:19]2[CH:24]=[N:23][C:22]([NH:25][CH2:26][CH2:27][CH2:28][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[N:21][C:20]=2[N:34]([CH:36]2[CH2:44][CH2:43][CH2:42][CH2:38][CH2:37]2)[CH:35]=1)=[O:14]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 685831992-(3-Imidazol-1-yl-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Produkt 1

HCID 160496602-(3-Imidazol-1-yl-propylamino)-8-cyclohexyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methoxy-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Triethylamine (0.5 mL) was added to a mixture of O-methylhydroxylamine hydrochloride (220 mg) and 2-(3-Imidazol-1-yl-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 28 Step F, 6.0 mg, 0.013 mmol) in 0.5 mL of methanol. The reaction mixture was kept in a sealed tube at 110° C. for 2 days with stirring. After cooling to room temperature, the solution was diluted with water and extracted with dichloromethane. The crude product, after concentration, was loaded to HPLC for purification (32 mL/min 5-100% MeCN/H2O gradient over 10 min). 2-(3-Imidazol-1-yl-propylamino)-8-cyclohexyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methoxy-amide was obtained as a white solid (4.3 mg, 70%). 1H NMR (400 MHz, CDCl3) δ (ppm): 12.02 (br, 1H), 9.26 (s, 1H), 8.75 (s, 1H), 7.32 (br, 1H), 7.10 (s, 1H), 6.95 (br, 1H), 5.82 (br, 1H), 5.06 (m, 1H), 4.10 (t, J=6.7 Hz, 2H), 3.88 (s, 3H), 3.51 (m, 2H), 2.20-1.20 (m, 12H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C21H27N7O3: 426.22 (M+H). Found: 426.2.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. concentrationThe crude product, after concentration
  3. customwas loaded to HPLC for purification (32 mL/min 5-100% MeCN/H2O gradient over 10 min)

Quellen und Nachweise

ORD-Eintrag
ord-875efa1e71a84f36936757e075bf886b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728003B2

Verknüpfte Notizen

Wird geladen…