Triethylamine → HCID 66628311, Verbindung

HRID 1046842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046842
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([O:20][C:21](=[O:53])[NH:22][C:23]1[N:52]=[C:26]2[N:27]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:51])([F:50])[F:49])[CH:43]=3)[C:28]([CH3:41])=[C:29]([C:39]#[N:40])[C@@H:30]([C:31]3[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=3)[N:25]2[N:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.C1COCC1>[CH2:13]([O:20][C:21](=[O:53])[N:22]([C:23]1[N:52]=[C:26]2[N:27]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:51])([F:49])[F:50])[CH:43]=3)[C:28]([CH3:41])=[C:29]([C:39]#[N:40])[C@@H:30]([C:31]3[CH:32]=[CH:33][C:34]([C:37]#[N:38])=[CH:35][CH:36]=3)[N:25]2[N:24]=1)[S:9]([CH3:8])(=[O:11])=[O:10])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70223867HCID 70223867, Verbindung

Produkt 1

HCID 66628311HCID 66628311, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon protective gas and at room temperature, triethylamine (11.1 mg, 140 mmol, 2.6 eq.) and methanesulfonyl chloride (41 mg, 360 mmol, 10 eq.) were added to a solution of benzyl{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}carbamate (20 mg, 36 mmol; Example 38) in dry pyridine (2 ml) and THF (2 ml), and the mixture was stirred for 12 h. The reaction mixture was then concentrated under reduced pressure and directly purified by preparative HPLC (Reprosil C18 column, 30×200 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (17.4 mg, 72% of theory).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customdirectly purified by preparative HPLC (Reprosil C18 column, 30×200 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (17.4 mg, 72% of theory)

Quellen und Nachweise

ORD-Eintrag
ord-613e886043164c128b125af9269b90b8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569314B2

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