1,2-Dichloroethane → HCID 57406926, compound

HRID 82853Notes

Reaction equation

HRID 82853 reaction equation
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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.[CH3:41][O:42][CH2:43][C:44]1[N:45]=[C:46]([CH2:49][N:50]2[N:54]=[C:53]([NH2:55])[CH:52]=[N:51]2)[O:47][CH:48]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:41][O:42][CH2:43][C:44]1[N:45]=[C:46]([CH2:49][N:50]2[N:54]=[C:53]([NH:55][C:9]([C:7]3[N:8]=[C:4]([CH3:3])[O:5][C:6]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11])[CH:52]=[N:51]2)[O:47][CH:48]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 156303442-Methyl-5-phenyl-1,3-oxazole-4-carboxylic acidHCID 67958086HCID 67958086, compound

Product 1

HCID 57406926HCID 57406926, compound

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-phenyloxazole-4-carboxylic acid (WO 2009/077990, p. 113) (955 mg, 4.70 mmol) in CH2Cl2 (27 mL) was treated at rt with DMAP (143 mg, 1.17 mmol), HOBt (763 mg, 5.65 mmol), EDC (2.25 g, 11.75 mmol) and DIPEA (3.22 mL, 18.80 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((4-(methoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (983 mg, 4.70 mmol) in CH2Cl2 (20 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (40 mL), the layers were separated and the org. phase was washed with water (40 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by crystallization for EA to give the title compound as a white solid: TLC: rf (4:6 hept-EA)=0.14. LC-MS-conditions 07: tR=0.84 min, [M+H]+=395.44.

Workup

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with water (40 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue
  8. customby crystallization for EA

Sources & evidence

ORD record
ord-baf7511a72d94cb7929451ef04486d3d
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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