Nitrogen → 2-Methyl-5-m-tolyl-oxazole-4-carboxylic acid [2-(5,5-difluoro-hexyl)-oxazol-4-yl]-amide

HRID 1189433Notes

Reaction equation

HRID 1189433 reaction equation
N#N.C(OC(=O)[N:9]([C:25]1[N:26]=[C:27]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:36])[CH3:35])[O:28][CH:29]=1)[C:10]([C:12]1[N:13]=[C:14]([CH3:24])[O:15][C:16]=1[C:17]1[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:37][C:34]([F:36])([CH3:35])[CH2:33][CH2:32][CH2:31][CH2:30][C:27]1[O:28][CH:29]=[C:25]([NH:9][C:10]([C:12]2[N:13]=[C:14]([CH3:24])[O:15][C:16]=2[C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)=[O:11])[N:26]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 67128661[2-(5,5-Difluoro-hexyl)-oxazol-4-yl]-(2-methyl-5-m-tolyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

Product 1

HCID 498397752-Methyl-5-m-tolyl-oxazole-4-carboxylic acid [2-(5,5-difluoro-hexyl)-oxazol-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(5,5-difluoro-hexyl)-oxazol-4-yl]-(2-methyl-5-m-tolyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester (32 mg, 0.06 mmol) in dry CH2Cl2 (1.0 mL) was treated at 0° C. with trifluoroacetic acid (0.05 mL, 0.65 mmol). After stirring at rt for 16 h, the reaction mixture was quenched with sat. aq. NaHCO3, extracted with CH2Cl2 (3×10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by HPLC gave the title compound as a light brown solid. TLC: rf (4:1 hept-EA)=0.21. LC-MS-conditions 02: tR=1.17 min, [M+H]+=404.43.

Workup

  1. customthe reaction mixture was quenched with sat. aq. NaHCO3
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by HPLC

Sources & evidence

ORD record
ord-15aa63ffa3bc4b74985f1530c8cb389b
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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