Ammonia → Rilpivirine

HRID 2280429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280429
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12](/[CH:16]=[CH:17]/[C:18]#[N:19])=[CH:11][C:10]=2[CH3:20])[CH:5]=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N>C(O)(C)C>[CH3:20][C:10]1[CH:11]=[C:12](/[CH:16]=[CH:17]/[C:18]#[N:19])[CH:13]=[C:14]([CH3:15])[C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[N:7]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 72721606HCID 72721606, Verbindung

Produkt 1

HCID 6451164RilpivirineAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
82.5 °C

Versuchsvorschrift

To a mixture of (E)-3-(4-(2-chloropyrimidin-4-ylamino)-3,5-dimethylphenyl)acrylonitrile (40 gm), 4-aminobenzonitrile (17 gm), isopropanol (400 ml) and p-toluenesulfonic acid (20 ml) were added at room temperature. The reaction mixture was then heated to 80 to 85° C. and stirred for 4 hours. The reaction mass was then cooled to 0° C. and pH was adjusted to 10 to 11 with aqueous ammonia solution. The separated solid was filtered and then dried to provide 40 gm of rilpivirine.

Aufarbeitung

  1. additionwere added at room temperature
  2. temperatureThe reaction mass was then cooled to 0° C.
  3. filtrationThe separated solid was filtered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2ae6918ee7b041b9abef86dac4a38581
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139535B2

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