1,2-Dichloroethane → N-(2-((2-(methoxymethyl)thiazol-4-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-4-carboxamide

HRID 82795Notes

Reaction equation

HRID 82795 reaction equation
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[S:44][CH:45]=[C:46]([CH2:48][N:49]2[N:53]=[C:52]([NH2:54])[CH:51]=[N:50]2)[N:47]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:40][O:41][CH2:42][C:43]1[S:44][CH:45]=[C:46]([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)[N:47]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 679580032-{[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl}-2H-1,2,3-triazol-4-amine

Product 1

HCID 86698197N-(2-((2-(methoxymethyl)thiazol-4-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-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 commercially available 5-phenyloxazole-4-carboxylic acid (42 mg, 0.21 mmol) in CH2Cl2 (3.0 mL) was treated at rt with DMAP (6.6 mg, 0.05 mmol), HOBt (36 mg, 0.26 mmol), EDC (102 mg, 0.53 mmol) and DIPEA (0.16 mL, 0.96 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((2-(methoxymethyl)thiazol-4-yl)methyl)-2H-1,2,3-triazol-4-amine (48 mg, 0.21 mmol) in CH2Cl2 (3.0 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (15.0 mL), the layers were separated and the org. phase was washed with 1N HCl (10.0 mL), water (5.0 mL), followed by brine (10.0 mL) and dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound as a white solid. TLC: rf (7:3 hept-EA)=0.15. LC-MS-conditions 07: tR=0.83 min, [M+H]+=397.23.

Workup

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with 1N HCl (10.0 mL), water (5.0 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (60:40 hept-EA)

Sources & evidence

ORD record
ord-5be7842f9e6f4d2399842f466b838ad0
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

Loading…