1,2-Dichloroethane → HCID 57407309, Verbindung

HRID 82856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82856
N#N.[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([OH:16])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[CH2:40]([O:42][CH2:43][C:44]1[N:45]=[C:46]([CH2:49][N:50]2[N:54]=[C:53]([NH2:55])[CH:52]=[N:51]2)[O:47][CH:48]=1)[CH3:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:40]([O:42][CH2:43][C:44]1[N:45]=[C:46]([CH2:49][N:50]2[N:54]=[C:53]([NH:55][C:14]([C:10]3[N:11]=[CH:12][O:13][C:9]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:16])[CH:52]=[N:51]2)[O:47][CH:48]=1)[CH3:41]

Komponenten

9

Edukt 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 679579762-((4-(Ethoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine

Produkt 1

HCID 57407309HCID 57407309, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 5-phenyloxazole-4-carboxylic acid (36 mg, 0.19 mmol) in CH2Cl2 (1.0 mL) was treated at rt with DMAP (5.8 mg, 0.05 mmol), HOBt (31 mg, 0.23 mmol), EDC (91 mg, 0.48 mmol) and DIPEA (0.13 mL, 0.76 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((4-(ethoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (43 mg, 0.19 mmol) in CH2Cl2 (0.9 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (10 mL) and the org. phase was washed with water (10 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (3:7 hept-EA) gave the title compound as a yellow oil: TLC: rf (7:3 hept-EA)=0.34. LC-MS-conditions 07: tR=0.84 min, [M+H]+=395.08.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight at rt
  2. washphase was washed with water (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (3:7 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-eee96bedacae48bebf467998be1ce56a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846733B2

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