1,2-Dichloroethane → HCID 67968164, compound

HRID 82799Notes

Reaction equation

HRID 82799 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[O:46][CH:47]=[C:48]([CH2:50][N:51]2[N:55]=[C:54]([NH2:56])[CH:53]=[N:52]2)[N:49]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:42][O:43][CH2:44][C:45]1[O:46][CH:47]=[C:48]([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)[N:49]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 679583082-((2-(methoxymethyl)oxazol-4-yl)methyl)-2H-1,2,3-triazol-4-amine

Product 1

HCID 67968164HCID 67968164, 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-(m-tolyl)oxazole-4-carboxylic acid (WO 2009/077990, p. 112) (14 mg, 0.06 mmol) in CH2Cl2 (0.3 mL) was treated at rt with DMAP (2 mg, 0.02 mmol), HOBt (10 mg, 0.08 mmol), EDC (31 mg, 0.16 mmol) and DIPEA (0.04 mL, 0.26 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((2-(methoxymethyl)oxazol-4-yl)methyl)-2H-1,2,3-triazol-4-amine (13 mg, 0.06 mmol) in CH2Cl2 (0.3 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (5 mL), the org. phase was washed with water (5 mL), dried over Na2SO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (1:2 hept-EA) gave the title compound as a colorless oil: TLC: rf (1:2 hept-EA)=0.36. LC-MS-conditions 07: tR=0.88 min, [M+H]+=408.69.

Workup

  1. stirringthe reaction mixture was stirred overnight at rt
  2. washphase was washed with water (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (1:2 hept-EA)

Sources & evidence

ORD record
ord-1c9f2a74133d4409bf61bc55c848a493
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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