Chloroform → HCID 57906599, Verbindung

HRID 420503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420503
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]=[C:11](N)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)[Cl:26]>>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]=[C:11]([Cl:26])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 6212ChloroformHCID 57906537HCID 57906537, Verbindung

Produkt 1

HCID 57906599HCID 57906599, VerbindungAusbeute 62 %

Versuchsvorschrift

A mixture of [2-amino-5-(2,4-dichloro-phenyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester (1.78 g, 4.82 mmol, prepared according to Example 6, Step 3.2), tBuONO (1.05 mL, 8.0 mmol), and CuCl2 (1.01 g, 7.51 mmol) in CHCl3 (6 mL) was stirred at RT for 3 days with exclusion of light. The reaction mixture was concentrated under vacuum, then the remaining residue was suspended in a 2.0 M aqueous Na2CO3 solution (200 mL) and extracted with AcOEt (2×100 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→4:6) to yield the title compound (1.17 g, 3.0 mmol, 62%) as a colorless solid. MS: 388 [M+1]+; HPLC: AtRet=2.89; TLC: RF 0.36 ([hexane/DCM 1:1]/TBME 95:5).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractionextracted with AcOEt (2×100 mL)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→4:6)

Quellen und Nachweise

ORD-Eintrag
ord-e0ee37d0c74f4088984a22bc15289a9f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097617B2

Notizen zur Reaktion

Wird geladen…