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

HRID 82794Notes

Reaction equation

HRID 82794 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[N:44]=[C:45]([CH2:48][N:49]2[N:53]=[C:52]([NH2:54])[CH:51]=[N:50]2)[S: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)[S:46][CH:47]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 679584992-((4-(methoxymethyl)thiazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine

Product 1

HCID 86698196N-(2-((4-(methoxymethyl)thiazol-2-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 (64 mg, 0.33 mmol) in CH2Cl2 (3.0 mL) was treated at rt with DMAP (10 mg, 0.08 mmol), HOBt (55 mg, 0.39 mmol), EDC (157 mg, 0.82 mmol) and DIPEA (0.25 mL, 1.48 mmol) and the resulting mixture was stirred for 15 min at rt. A solution of 2-((4-(methoxymethyl)thiazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (74 mg, 0.33 mmol) in CH2Cl2 (3.5 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 (15.0 mL), water (10.0 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 (gradient from 90:10 hept-EA to 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]+=397.21

Workup

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with 1N HCl (15.0 mL), water (10.0 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (gradient from 90:10 hept-EA to 60:40 hept-EA)

Sources & evidence

ORD record
ord-fadbd8727083449f8e061052f7efbd62
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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