Tetrahydrofuran-3-carbonyl chloride → N-{(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}tetrahydrofuran-3-carboxamide

HRID 2200957

Reaktionsgleichung

Reaktionsgleichung von HRID 2200957
Cl.[NH2:2][C:3]1[N:32]=[C:6]2[N:7]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:8]([CH3:21])=[C:9]([C:19]#[N:20])[C@@H:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[N:5]2[N:4]=1.[O:33]1[CH2:37][CH2:36][CH:35]([C:38](Cl)=[O:39])[CH2:34]1>N1C=CC=CC=1>[C:19]([C:9]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:5]2[N:4]=[C:3]([NH:2][C:38]([CH:35]3[CH2:36][CH2:37][O:33][CH2:34]3)=[O:39])[N:32]=[C:6]2[N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[CH:23]=2)[C:8]=1[CH3:21])#[N:20]

Komponenten

4

Edukt 2

HCID 14020412Tetrahydrofuran-3-carbonyl chlorideHCID 66627899(7R)-2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile hydrochloride

Produkt 1

HCID 46841345N-{(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}tetrahydrofuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon protective gas, (7R)-2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile hydrochloride (30 mg, 66 μmol) was dissolved in abs. pyridine (1.5 ml). At room temperature, tetrahydrofuran-3-carbonyl chloride (26 mg, 197 μmol, 3 eq.) was added. After 12 h, analysis of the reaction by HPLC showed substantial conversion. The reaction mixture was concentrated under reduced pressure and purified by preparative HPLC (Reprosil C18 column, 250×30 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (21.1 mg, 62% of theory).

Aufarbeitung

  1. customanalysis of the reaction by HPLC
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by preparative HPLC (Reprosil C18 column, 250×30 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (21.1 mg, 62% of theory)

Quellen und Nachweise

ORD-Eintrag
ord-6781dd9d9f22483db1566018d0edf255
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359362B2

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