HCID 59568585, Verbindung → HCID 49783984, Verbindung

HRID 216972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216972
[C:1]([C@@H:3]([NH:27][C:28]([C:30]1([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:36][C:30]1([C:28]([NH:27][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[CH:13][C:14]([S:17]([N:20]4[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]4)(=[O:18])=[O:19])=[CH:15][CH:16]=3)=[CH:9][CH:10]=2)=[O:29])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Komponenten

3

Edukt 1

HCID 59568585HCID 59568585, Verbindung

Produkt 1

HCID 49783984HCID 49783984, VerbindungAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 4-(1-cyano-2-(4′-(4-methylpiperazin-1-ylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 29, step (ii), 250 mg) in formic acid (2 mL) was heated at 50° C. for 20 min. Volatiles were removed under reduced pressure and then azeotroped with methanol. The product was purified by reversed phase HPLC using methanol in 0.1% aqueous TFA as eluent. The residue was converted to the free base by elution through a PL-HCO3 MP cartridge in dichloromethane/methanol to afford the titled compound (43 mg).

Aufarbeitung

  1. customVolatiles were removed under reduced pressure
  2. customazeotroped with methanol
  3. customThe product was purified by reversed phase
  4. washThe residue was converted to the free base by elution through a PL-HCO3 MP cartridge in dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-2958ae81ec7340fa9ac4497958f20ba2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

Notizen zur Reaktion

Wird geladen…