Water → HCID 18510705, compound

HRID 1370258Notes

Reaction equation

HRID 1370258 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH:7]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH:17]2[O:21][N:20]=[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:18]2)=[O:16])=[CH:10][CH:9]=1.C(N(C(C)C)C(C)C)C.O>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][CH:7]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([CH:17]2[O:21][N:20]=[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:18]2)=[O:16])=[CH:12][CH:13]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 18510678HCID 18510678, compound

Product 1

HCID 18510705HCID 18510705, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

) A solution of chloroacetylchloride (0.0089 mol) in CH2Cl2 (20 ml, dried over MgSO4) was added to a cooled solution of (±)-N-[4-(aminophenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (0.0081 mol) and N-ethyl-N-(1-methylethyl)-2-propanamine (0.0093 mol) in CH2Cl2 (100 ml). The reaction mixture was stirred for one hour at 0° C. Water was added. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue (crude oil) was purified by short column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated under reduced pressure. The residue was stirred in EtOAc. The precipitate was filtered off, washed with EtOAc, and dried, yielding 2.47 g (68%) of (±)-N-[4-[[(chloroacetyl)amino]phenylmethyl]phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide. (compound 127)

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue (crude oil) was purified by short column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated under reduced pressure
  8. stirringThe residue was stirred in EtOAc
  9. filtrationThe precipitate was filtered off
  10. washwashed with EtOAc
  11. customdried

Sources & evidence

ORD record
ord-eaa49bbf6d874efe9ef5c48a5e3f4108
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

Loading…