Hexamethylenetetramine → HCID 59504651, compound

HRID 2400597Notes

Reaction equation

HRID 2400597 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([C:17]3[CH:21]=[C:20]([CH3:22])[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[N:18]=3)[O:14][N:13]=2)=[CH:8][CH:7]=1)=[O:4].[CH2:31]1N2CN3CN(C2)C[N:32]1C3.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:22][C:20]1[N:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[N:18]=[C:17]([C:15]2[O:14][N:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([N:5]4[C:3](=[O:4])[CH2:2][NH:32][CH2:31]4)=[CH:7][CH:8]=3)[N:16]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 4101HexamethylenetetramineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59504686HCID 59504686, compound

Product 1

HCID 59504651HCID 59504651, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-N-(4-{5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetamide (Step 2, 190 mg, 0.407 mmol) in ethanol (4 mL) was added hexamethylenetetramine (286 mg, 2.04 mmol). The reaction mixture was stirred and heated at reflux for 2.5 h. After being cooled to rt, the solvent was evaporated, and the residue was subjected to preparative HPLC. The crude product thus obtained was treated with a mixture of ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate. Subsequent filtration and evaporation of the solvent yielded the title compound which was obtained in pure form after stirring with cyclohexane (84 mg, 50%): 1H NMR (400 MHz, CDCl3) δ 8.23 (d, 2H), 7.70 (d, 2H), 7.13 (d, 2H), 7.07 (d, 2H), 6.79 (s, 1H), 5.40 (s, 2H), 4.92 (s, 2H), 3.69 (s, 2H), 2.32 (s, 3H), 2.25 (s, 3H); ES-MS m/z 415, HPLC RT (Method E) 1.62 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. customthe solvent was evaporated
  4. customThe crude product thus obtained
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. filtrationSubsequent filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-5c1600af3a5f4f9c94461bcdca3146cc
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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