Sodium Carbonate → HCID 53846173, compound

HRID 1459466Notes

Reaction equation

HRID 1459466 reaction equation
S(O[CH2:6][CH:7]1[O:11][CH2:10][CH2:9][CH2:8]1)(=O)(=O)C.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]2[N:23]=[C:22]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[O:21][N:20]=2)[C:16]([O:30][CH3:31])=[CH:15][C:14]=1[NH2:32].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([C:19]2[N:23]=[C:22]([CH:24]3[CH2:25][CH2:26][N:27]([CH2:6][CH:7]4[CH2:8][CH2:9][CH2:10][O:11]4)[CH2:28][CH2:29]3)[O:21][N:20]=2)[C:16]([O:30][CH3:31])=[CH:15][C:14]=1[NH2:32]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 266119(Tetrahydrofuran-2-yl)methyl methanesulfonate2×HCID 54301968HCID 54301968, compound

Product 1

HCID 53846173HCID 53846173, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of tetrahydrofurfuryl mesylate (2.34 g), intermediate 12 (2.7 g) and sodium carbonate (2.8 g) in 4-methyl-2-pentanone (180 ml) was stirred and refluxed for 24 hours. More tetrahydrofurfuryl mesylate (1 g) was added and the reaction mixture was stirred and refluxed for 24 hours. The reaction mixture was cooled, washed with water, dried over MgSO4, filtered and the filtrate evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding of 1.34 g (39%) 2-chloro-5-methoxy-4-[5-[1 -[(tetrahydro-2-furanyl)methyl]-4-piperidinyl]- 1,2,4-oxadiazol-3-yl]-benzenamine (compound 7; mp. 148.5° C.).

Workup

  1. temperaturerefluxed for 24 hours
  2. stirringthe reaction mixture was stirred
  3. temperaturerefluxed for 24 hours
  4. temperatureThe reaction mixture was cooled
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  10. customThe pure fractions were collected
  11. customthe solvent evaporated
  12. customThe residue was crystallized from CH3CN
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-aca0b19b55084bf2be4c721d508961f8
Source dataset
uspto-grants-1998_12
Patent number
US05854261

Reaction notes

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