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Ammonium formate → N'-[5-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea

HRID 351228
Notes
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Reaction equation

HRID 351228 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([NH:28][C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.C1COCC1.O.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([NH:28][C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH:16]=2)=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 21091147N'-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea

Product 1

HCID 135737387N'-[5-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N,N-dimethylureaYield 58.6%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 23938PalladiumSolvent

Procedure

To a solution of N′-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea (1.19 g) in EtOH (10 ml) and THF (10 ml) were added a solution of ammonium formate (509 mg) in H2O (2 ml) and 10% Pd-C 50% wet (150 mg). The mixture was refluxed for 1 hour. The catalyst was filtered off through a celite pad and the pad was washed with EtOH. The filtrate and combined washings were concentrated in vacuo. To the residue were added AcOEt and H2O. White precipitates were appeared and collected and washed with H2O and IPE successively to give N′-[5-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea (555 mg) as a white powder.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. filtrationThe catalyst was filtered off through a celite pad
  3. washthe pad was washed with EtOH
  4. concentrationwere concentrated in vacuo
  5. additionTo the residue were added AcOEt and H2O
  6. customWhite precipitates
  7. customcollected
  8. washwashed with H2O and IPE successively

Sources & evidence

ORD record
ord-45fd2b08cd8c443a83219e1351c0986b
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07183306B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes