Dimethylamine → HCID 178489126, compound

HRID 895359Notes

Reaction equation

HRID 895359 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH:18][N:19]=[C:20]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)=[N:23][NH:22][C:21]2=[O:35])=[CH:8][CH:7]=1.[CH3:36][NH:37][CH3:38]>>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([C:24]2[C:20](=[N:19][NH:18][C:9]3[CH:10]=[C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:37]([CH3:38])[CH3:36])=[CH:7][CH:8]=3)[C:21](=[O:35])[NH:22][N:23]=2)[CH:30]=[CH:29][C:28]=1[O:31][CH3:32]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 178489125HCID 178489125, compound

Product 1

HCID 178489126HCID 178489126, compound

Conditions

Temperature
50 °C

Procedure

5-(3,4-Dimethoxy-phenyl)-4-{[6-(3-dimethylamino-propoxy)-biphenyl-3-yl]-hydrazono}-2,4-dihydro-pyrazol-3-one (compound 121) was prepared by dissolving 4-{[6-(3-bromo-propoxy)-biphenyl-3-yl]-hydrazono}-5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (s) in 1 mL of a dimethylamine solution (2 M in THF) and heating to 50° C. for one hour. The solvent was then evaporated and the residue was purified by silica gel chromatography (eluent: 10% methanol/DCM) to afford 6 mg product (compound 121): HPLC (Rt): 5.490 minutes; m/e: 501.23, MS (ES+): 502.2.

Workup

  1. custom5-(3,4-Dimethoxy-phenyl)-4-{[6-(3-dimethylamino-propoxy)-biphenyl-3-yl]-hydrazono}-2,4-dihydro-pyrazol-3-one (compound 121) was prepared
  2. customThe solvent was then evaporated
  3. customthe residue was purified by silica gel chromatography (eluent: 10% methanol/DCM)

Sources & evidence

ORD record
ord-e7aee756366b450183622a26a583e879
Source dataset
uspto-grants-2005_07
Patent number
US06916798B2

Reaction notes

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