HCID 76492969, compound → HCID 53673207, compound

HRID 1279202Notes

Reaction equation

HRID 1279202 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[C:24](=[O:25])[N:23]([CH:26]([CH3:33])[CH:27]([NH:29]C(=O)C)[CH3:28])[N:22]=[CH:21]4)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>Cl>[NH2:29][CH:27]([CH3:28])[CH:26]([N:23]1[C:24](=[O:25])[N:20]([C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)=[CH:19][CH:18]=2)[CH:21]=[N:22]1)[CH3:33]

Participants

3

Reactant 1

HCID 76492969HCID 76492969, compound

Product 1

HCID 53673207HCID 53673207, compoundYield 0.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of intermediate (3d) (0.0069 mol) in HCl conc. (50 ml) was stirred and refluxed for 48 hours. The solvent was evaporated and the residue was dissolved in H2O (50ml). The mixture was alkalized with NH4OH and extracted with CH2Cl2/CH3OH 80/20 (500 ml). The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was triturated in 2-propanol, filtered off and dried, yielding 2.6 g (92%) of [R(R*,S*)]-2-(2-amino-1-methylpropyl)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (interm. 4; mp. 237.2° C.; [α]20D=+1.010° @19.79 mg/2ml in DMF).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in H2O (50ml)
  4. extractionextracted with CH2Cl2/CH3OH 80/20 (500 ml)
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was triturated in 2-propanol
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-3f08130c8966485b938900103c96fb67
Source dataset
uspto-grants-2002_09
Patent number
US06448244B1

Reaction notes

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