Sodium periodate → Methyl (4-{3-cyano-4-formyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}pyridin-2-yl)carbamate

HRID 2401827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401827
[C:1]([C:3]1[C:7]([CH:8]([OH:11])CO)=[C:6]([C:12]2[N:16]=[CH:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:13]=2)[S:5][C:4]=1[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:33])[O:31][CH3:32])[CH:24]=1)#[N:2].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O>[C:1]([C:3]1[C:7]([CH:8]=[O:11])=[C:6]([C:12]2[N:16]=[CH:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:13]=2)[S:5][C:4]=1[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:33])[O:31][CH3:32])[CH:24]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 23667635Sodium periodate2×HCID 68100371Methyl (4-{3-cyano-4-(1,2-dihydroxyethyl)-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}pyridin-2-yl)carbamate

Produkt 1

HCID 86667481Methyl (4-{3-cyano-4-formyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}pyridin-2-yl)carbamateAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl (4-{3-cyano-4-(1,2-dihydroxyethyl)-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}pyridin-2-yl)carbamate (0.362 g, 0.769 mmol) was dissolved in acetone (40 mL) and water (10 mL). Sodium metaperiodate (0.494 g, 2.31 mmol) was added and the mixture was stirred at room temperature for 6 hours. Sodium metaperiodate (0.329 g, 1.54 mmol) was added and the mixture was stirred for 16 more hours. The mixture was concentrated in rotavapor. The residue was triturated with water, filtered and washed thoroughly with water, then dried in lyophilizer to give a dry solid product (0.320 g, yield 94.8%). LC/MS: (FA) ES+ 439. 1H NMR (400 MHz, d6-dmso) δ 10.67 (s, 1H), 10.57 (s, 1H), 9.05 (s, 1H), 8.49 (m, 1H), 8.28 (s, 1H), 7.50 (m, 1H), 5.69-5.73 (m, 1H), 3.94-3.98 (m, 1H), 3.73 (s, 3H), 3.66-3.71 (m, 1H), 1.93-2.12 (m, 3H), 1.58-1.71 (m, 3H).

Aufarbeitung

  1. stirringthe mixture was stirred for 16 more hours
  2. concentrationThe mixture was concentrated in rotavapor
  3. customThe residue was triturated with water
  4. filtrationfiltered
  5. washwashed thoroughly with water
  6. customdried in lyophilizer

Quellen und Nachweise

ORD-Eintrag
ord-1b4dc2917b954f19887ae4431cb6f862
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796268B2

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