Water → HCID 18510698, compound

HRID 2219095Notes

Reaction equation

HRID 2219095 reaction equation
CS(Cl)(=O)=O.O[C:7]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH:24]2[O:28][N:27]=[C:26]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[CH2:25]2)=[O:23])=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8].C(N(CC)CC)C.O>C(Cl)Cl>[C:9]1([C:7]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([CH:24]3[O:28][N:27]=[C:26]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[CH2:25]3)=[O:23])=[CH:19][CH:20]=2)=[CH2:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18510681HCID 18510681, compound

Product 1

HCID 18510698HCID 18510698, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

) Methanesulfonyl chloride (0.010 mol) was added to a solution of compound (51) (0.005 mol) and triethylamine (0.013 mol) in CH2Cl2 (100 ml, dried over MgSO4), stirred at 0° C. The resulting reaction mixture was stirred for 1 hour at 10° C. Water was added. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by short column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated under reduced pressure. The residue was crystallized from EtOAc. The precipitate was filtered off, washed with EtOAc, then dried, yielding 0.5 g (27%) of (±)4,5-dihydro-N-[4-(1-phenylethenyl)phenyl]-3-(3-pyridinyl)-5-isoxazolecarboxamide (compound 378).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 1 hour at 10° C
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by short column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was crystallized from EtOAc
  11. filtrationThe precipitate was filtered off
  12. washwashed with EtOAc
  13. customdried

Sources & evidence

ORD record
ord-94b355b7a1cb4443a01c20ccf8add477
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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