Hydrochloric Acid → HCID 86590906, compound

HRID 1370261Notes

Reaction equation

HRID 1370261 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH2:12][CH:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:23](O)=[O:24])=[CH:18][CH:17]=3)=[O:14])[O:10][N:9]=2)[CH:3]=1>C(Cl)Cl>[Cl:1][C:23]([CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13]([CH:11]2[O:10][N:9]=[C:8]([C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)[CH2:12]2)=[O:14])=[CH:17][CH:18]=1)=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18510724HCID 18510724, compound

Product 1

HCID 86590906HCID 86590906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

) HCl (gaseous) (excess) was bubbled through a suspension of (±)-4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]-a-phenylbenzeneacetic acid (0.005 mol) in CH2Cl2 (100 ml) for 10 minutes. The solvent was removed under reduced pressure. The white solid was co-evaporated twice with toluene. Thionyl chloride (50 ml) was added. The reaction mixture was heated and refluxed for 1 hour. The solvent was evaporated. The reaction mixture was co-evaporated three times with toluene, yielding N-[4-[(chlorocarbonyl)phenylmethyl]phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (compound 493).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThionyl chloride (50 ml) was added
  3. temperatureThe reaction mixture was heated
  4. temperaturerefluxed for 1 hour
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c651252bfead45cfa75613b2729f7300
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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