Pyrrolidine → HCID 11516079, compound

HRID 1445819Notes

Reaction equation

HRID 1445819 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:21][CH2:22]OS(C)(=O)=O.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:21][CH2:22][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86614641HCID 86614641, compound

Product 1

HCID 11516079HCID 11516079, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methanesulfonic acid 2-{5-methyl-2-[4-(pyridin-2-ylmethoxy)-phenyl]-oxazol-4-yl}-ethyl ester (0.85 mmol) and pyrrolidine (0.71 mL, 8.5 mmol) in THF (4 mL) is heated at reflux overnight. The mixture is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc (2×), and the combined organic phase is washed with brine and dried (NaSO4). After the solvent is removed, the residue is purified by flash chromatography chromatography [40 g SiO2, elute 20% (10% 2 M NH3 in MeOH/90% CH2Cl2): 80% CH2Cl2 to 70% (10% 2 M NH3 in MeOH/90% CH2Cl2): 30% CH2Cl2] to yield the title compound. MS (m/e): 364.2 (M+1)

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. customThe mixture is partitioned between EtOAc and water
  4. extractionThe aqueous phase is extracted with EtOAc (2×)
  5. washthe combined organic phase is washed with brine
  6. dry with materialdried (NaSO4)
  7. customAfter the solvent is removed
  8. customthe residue is purified by flash chromatography chromatography [40 g SiO2, elute 20% (10% 2 M NH3 in MeOH/90% CH2Cl2): 80% CH2Cl2 to 70% (10% 2 M NH3 in MeOH/90% CH2Cl2): 30% CH2Cl2]

Sources & evidence

ORD record
ord-75483fb0b65a4653be489462070eb549
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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