1,2-Dichloroethane → N-(2-((4-acetyloxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

HRID 82800Notes

Reaction equation

HRID 82800 reaction equation
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.[NH2:42][C:43]1[CH:47]=[N:46][N:45]([CH2:48][C:49]2[O:50][CH:51]=[C:52]([C:54](=[O:56])[CH3:55])[N:53]=2)[N:44]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:54]([C:52]1[N:53]=[C:49]([CH2:48][N:45]2[N:44]=[C:43]([NH:42][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:47]=[N:46]2)[O:50][CH:51]=1)(=[O:56])[CH3:55]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 67365588HCID 67365588, compound

Product 1

HCID 67967926N-(2-((4-acetyloxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

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) (590 mg, 2.72 mmol) in CH2Cl2 (20 mL) was treated at rt with DMAP (82 mg, 0.68 mmol), HOBt (441 mg, 3.62 mmol), EDC (1.3 g, 6.79 mmol) and DIPEA (1.8 mL, 10.86 mmol) and the resulting mixture was stirred for 30 min at rt. A solution of 1-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)ethanone (WO 2009/077990, p. 105) (562 mg, 2.72 mmol) in CH2Cl2 (7.0 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (50 mL), the org. phase was washed with water (50 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 white solid: TLC: rf (4:6 hept-EA)=0.35. LC-MS-conditions 07: tR=0.88 min, [M+H]+=407.05.

Workup

  1. stirringthe reaction mixture was stirred overnight at rt
  2. washphase was washed with water (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (4:6 hept-EA)

Sources & evidence

ORD record
ord-fb7e4b9163634ffc8ba7be72eabedeb3
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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