Ammonia → HCID 178508629, Verbindung

HRID 244162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244162
[NH3:1].Cl[C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@H:13]3[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1.C(=O)=O.CC(C)=O>O1CCOCC1.CC(O)C>[NH2:1][C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@H:13]3[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 18522661Acetone cardiceHCID 178521038HCID 178521038, Verbindung

Produkt 1

HCID 178508629HCID 178508629, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Gaseous ammonia (from a lecture bottle) was condensed into a suspension of trans-[3-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol (172.6 mg, 0.475 mmol) in dioxane (3 mL) and iPrOH (3 mL) in a sealable glass tube, cooled by dry ice/acetone, until the volume increased by ≈2 mL, then the tube was sealed and heated to 90° C. overnight. The solvents were evaporated, water was added to the residue, and the pale yellow solid was filtered off and dried in vacuo to give the title compound as a pale yellow solid. The compound was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 2.41-2.52 (m, 2H), 2.52-2.64 (m, 3H), 3.83 (d, J=6.3 Hz, 2H), 5.30-5.40 (m, 1H), 5.60 (brs, 2H), 7.29 (s, 1H), 8.26 (s, 1H). MS (ES+): m/z 345.1 (100) [MH+]. HPLC: tR=1.9 min (OpenLynx, polar—5 min).

Aufarbeitung

  1. customcondensed
  2. temperatureincreased by ≈2 mL
  3. customthe tube was sealed
  4. customThe solvents were evaporated
  5. additionwater was added to the residue
  6. filtrationthe pale yellow solid was filtered off
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee2d5976981f4bb280e5f25ff3bec203
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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