Triethylamine → 6-(3-(1H-imidazol-2-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine

HRID 1049924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049924
[NH2:1][C:2]1[C:3]2[N:11]=[C:10](C3C=C(C=C(F)C=3)C(NCC3CCN(C)CC3)=O)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1.C(N(CC)CC)C.CC(N(C)C)=O>ClCCl>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:10]2[CH:9]=[CH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[N:11]=2)[CH2:37]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 679965363-(1H-imidazol-2-yl)piperidine hydrochlorideHCID 727035233-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-((1-methylpiperidin-4-yl)methyl)benzamide

Produkt 1

HCID 727039236-(3-(1H-imidazol-2-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amineAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To an 8 mL screw-cap vial was added 6-chloropyrido[3,2-d]pyrimidin-4-amine 10 (1 equiv., 0.68 mmol, 123 mg), 3-(1H-imidazol-2-yl)piperidine hydrochloride (1 equiv., 0.68 mmol, 128 mg), triethylamine (3 equiv., 2.05 mmol, 0.287 mL) and DMA (2 mL). The reaction was capped and shaken at 100° C. overnight. The reaction was then cooled to room temperature, diluted with dichloromethane, and washed with water. The organic was then concentrated, then purified by reverse phase HPLC, yielding 16 mg of product. 1H NMR (400 MHz, DMSO) δ 8.20-8.14 (m, 3H), 7.82-7.77 (m, 1H), 7.54-7.49 (d, J=9.4 Hz, 1H), 7.38-7.28 (d, J=8.1 Hz, 2H), 6.96-6.94 (s, 2H), 4.79-4.71 (d, J=12.7 Hz, 1H), 4.53-4.46 (d, J=17.4 Hz, 1H), 3.17-3.07 (m, 1H), 3.07-2.96 (m, 1H), 2.96-2.84 (m, 1H), 2.18-2.08 (m, 1H), 1.91-1.77 (m, 2H), 1.66-1.51 (m, 1H). LCMS M/Z (M+H)=296.

Aufarbeitung

  1. customTo an 8 mL screw-cap vial
  2. customThe reaction was capped
  3. temperatureThe reaction was then cooled to room temperature
  4. washwashed with water
  5. concentrationThe organic was then concentrated
  6. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-eb9212c002f64c099a0e8fde9506ae6f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382241B2

Notizen zur Reaktion

Wird geladen…