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

HRID 82790Notes

Reaction equation

HRID 82790 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.[CH3:42][O:43][CH2:44][C:45]1[S:46][C:47]([CH2:50][N:51]2[N:55]=[C:54]([NH2:56])[CH:53]=[N:52]2)=[CH:48][N:49]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:42][O:43][CH2:44][C:45]1[S:46][C:47]([CH2:50][N:51]2[N:55]=[C:54]([NH:56][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:53]=[N:52]2)=[CH:48][N:49]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 679581002-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-amine

Product 1

HCID 67968178N-(2-((2-(Methoxymethyl)thiazol-5-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) (70.0 mg, 0.32 mmol) in CH2Cl2 (1.5 mL) was treated at rt with DMAP (9.8 mg, 0.08 mmol), HOBt (52 mg, 0.39 mmol), EDC (154 mg, 0.81 mmol) and DIPEA (0.22 mL, 1.3 mmol) and the resulting mixture was stirred for 30 min at rt. A solution of 2-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-amine (73 mg, 0.32 mmol) in CH2Cl2 (1.5 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (5.0 mL), the layers were separated and the org. phase was washed with water (5.0 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 colorless oil: TLC: rf (4:6 hept-EA)=0.29. LC-MS-conditions 07: tR=0.94 min, [M+H]+=425.09.

Workup

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with water (5.0 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)

Sources & evidence

ORD record
ord-ef29e5e15e4d4eb08e1419593a2ad64f
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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