1,2-Dichloroethane → HCID 57407307, Verbindung

HRID 82854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82854
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.[CH3:40][O:41][CH2:42][C:43]1[N:44]=[C:45]([CH2:48][N:49]2[N:53]=[C:52]([NH2:54])[CH:51]=[N:50]2)[O:46][CH:47]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:40][O:41][CH2:42][C:43]1[N:44]=[C:45]([CH2:48][N:49]2[N:53]=[C:52]([NH:54][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:51]=[N:50]2)[O:46][CH:47]=1

Komponenten

9

Edukt 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 679580862-((4-(Methoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine

Produkt 1

HCID 57407307HCID 57407307, 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 (50 mg, 0.26 mmol) in CH2Cl2 (1.3 mL) was treated at rt with DMAP (8 mg, 0.07 mmol), HOBt (43 mg, 0.32 mmol), EDC (127 mg, 0.67 mmol) and DIPEA (0.18 mL, 1.06 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((4-(methoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (55 mg, 0.26 mmol) in CH2Cl2 (1.3 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (5 mL), the layers were separated and the org. phase was washed with water (5 mL), dried over Na2SO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (4:6 hept-EA) gave the title compound as a white solid: TLC: rf (4:6 hept-EA)=0.13. LC-MS-conditions 07: tR=0.81 min, [M+H]+=381.14.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with water (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (4:6 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-3dc2a3d4851943bebfc464aabc5f2e48
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846733B2

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