Hydrochloric Acid → US9433622, Dmx-36

HRID 55864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55864
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:12]([CH:15]=2)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[N:24][N:25]([CH2:27][CH2:28][OH:29])[CH:26]=1.Cl>O1CCOCC1>[OH:29][CH2:28][CH2:27][N:25]1[CH:26]=[C:22]([NH:21][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][C:11]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[C:12]([CH:15]=3)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=2)[CH:23]=[N:24]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 90357141HCID 90357141, Verbindung

Produkt 1

HCID 78322872US9433622, Dmx-36

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-(2-Chloro-pyrimidin-4-yl)-2-pyrrolidin-1-yl-nicotinonitrile (9) (31 mg, 0.108 mmol) and 2-(4-amino-pyrazol-1-yl)-ethanol (32 mg, 0.252 mmol) were dissolved in 1,4-dioxane (1 mL). 4N HCl in 1,4-dioxane (30 μL, 0.120 mmol) was added and the mixture was heated at 140° C. in the microwave (250 W, stirring) for 90 minutes. The solvent was evaporated in vacuo and the residue dissolved in DMSO (1 mL). The crude product was purified twice by reversed phase preparative LC-MS. Fractions containing desired product were combined and the solvents evaporated in vacuo. The title compound was obtained as a yellow solid (3.7 mg, 9%); LCMS, Rt=7.43 min (Method C), m/z 377 (MH+).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in DMSO (1 mL)
  3. customThe crude product was purified twice by reversed phase preparative LC-MS
  4. additionFractions containing desired product
  5. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b9b79ddf853e4b708f731fbf8da6add9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433622B2

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