Water → HCID 58497414, compound

HRID 2175187Notes

Reaction equation

HRID 2175187 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([C:14](=[CH2:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH3:13].N12CCCN=C1CCCCC2.O>CN(C=O)C.CCOC(C)=O>[CH2:18]([O:17][C:15](=[O:16])[CH:14]([CH2:20][NH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH2:11][CH2:12][CH3:13])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 778873-Nitropyridin-2-ylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11844669Ethyl 2-propylacrylate

Product 1

HCID 58497414HCID 58497414, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-amino-3-nitropyridine (390 mg, 2.80 mmol) in DMF (3 ml) was added ethyl 2-propylacrylate (500 mg, 3.52 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (30 μl). The mixture was warmed to 80° C. and monitored by TLC (silica gel, 30% EtOAc/hexanes). After 48 hours, only starting material was detected by TLC. The reaction mixture was warmed to 100° C. for 4 days and cooled to room temperature. The reaction was poured into water and EtOAc. The layers were separated and the aqueous phase was extracted once more with EtOAc. The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 15-50% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give 90 mg (11%) of the desired compound which was used without further purification.

Workup

  1. temperatureThe reaction mixture was warmed to 100° C. for 4 days
  2. temperaturecooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted once more with EtOAc
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified via silica gel flash column chromatography (Companion, 12 g silica gel, 15-50% EtOAc/hexanes)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-be1870efaac240b383319ae19885d4e5
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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