1,2-Dichloroethane → HCID 57406925, Verbindung

HRID 82851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82851
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[C:7]([C:9]([OH:11])=O)[N:8]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[CH3:42][O:43][C:44]([C:47]1[N:48]=[C:49]([CH2:52][N:53]2[N:57]=[C:56]([NH2:58])[CH:55]=[N:54]2)[O:50][CH:51]=1)([CH3:46])[CH3:45]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:42][O:43][C:44]([C:47]1[N:48]=[C:49]([CH2:52][N:53]2[N:57]=[C:56]([NH:58][C:9]([C:7]3[N:8]=[C:4]([CH3:3])[O:5][C:6]=3[C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=3)=[O:11])[CH:55]=[N:54]2)[O:50][CH:51]=1)([CH3:46])[CH3:45]

Komponenten

9

Edukt 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 67958057HCID 67958057, Verbindung

Produkt 1

HCID 57406925HCID 57406925, 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 2-methyl-5-(m-tolyl)oxazole-4-carboxylic acid (WO 2009/077990, p. 112) (40.0 mg, 0.18 mmol) in CH2Cl2 (1.0 mL) was treated at rt with DMAP (5.6 mg, 0.05 mmol), HOBt (29.9 mg, 0.22 mmol), EDC (88.3 mg, 0.46 mmol) and DIPEA (0.13 mL, 0.74 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((4-(2-methoxypropan-2-yl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (43.7 mg, 0.18 mmol) in CH2Cl2 (0.8 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (2.0 mL), the layers were separated and the org. phase was washed with water (2.0 mL), dried over MgSO4, 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 colorless oil: TLC: rf (4:6 hept-EA)=0.35. LC-MS-conditions 06: tR=0.94 min, [M+H]+=437.34.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with water (2.0 mL)
  4. dry with materialdried over MgSO4
  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-f0dc5ca917b34229a1ae9b96fee3dc38
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846733B2

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