HCID 21873424, compound → HCID 21873309, compound

HRID 723350Notes

Reaction equation

HRID 723350 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:31][CH:32](OC)OC)[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[CH:21][CH:20]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[CH3:29][N:28]([CH3:30])[CH2:27][CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([N:18]2[CH:32]=[CH:31][N:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:16]2=[O:17])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 21873424HCID 21873424, compound

Product 1

HCID 21873309HCID 21873309, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(4-benzyloxyphenyl)-1-(2,2-dimethoxyethyl)-3-[4-(2-dimethylaminoethoxy)phenyl]urea (4.9 g), palladium (10% on carbon, 1.0 g) and ethanol (40 mL) was stirred under hydrogen for 5 hours. The catalyst was filtered off and the filtrate was concentrated. The residue was taken up in trifluoroacetic acid (20 mL) and the solution was stirred for 48 hours. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution. The organic phase was dried and concentrated. The solid residue was stirred with acetonitrile, and the product was filtered off. The product with the molecular weight of 339.40 (C19H21N3O3); MS (ESI): 340 ([M+H]+), was obtained in this way.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. stirringthe solution was stirred for 48 hours
  4. additionThe reaction mixture was diluted with dichloromethane
  5. washwashed with saturated sodium bicarbonate solution
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. stirringThe solid residue was stirred with acetonitrile
  9. filtrationthe product was filtered off
  10. customMS (ESI): 340 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-9661ab2c03ed4395ad720f22b0031616
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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