6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide → 1-(5-Benzoyl-4-(phenylamino)pyridin-2-yl)-3-ethylurea

HRID 2174243Notes

Reaction equation

HRID 2174243 reaction equation
[CH2:1]([NH:3][C:4](=[O:25])[NH:5][C:6]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]([C:10](N(OC)C)=[O:11])=[CH:8][N:7]=1)[CH3:2].[C:26]1([Mg]Br)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.C(Cl)Cl>[C:10]([C:9]1[C:16]([NH:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][C:6]([NH:5][C:4]([NH:3][CH2:1][CH3:2])=[O:25])=[N:7][CH:8]=1)(=[O:11])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 896503736-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamideHCID 178418255HCID 178418255, compound

Product 1

HCID 716223441-(5-Benzoyl-4-(phenylamino)pyridin-2-yl)-3-ethylureaYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 83 (15 mg, 0.044 mmol) was dissolved in dry THF (0.8 mL) and this solution added to the phenyl magnesium bromide (1M, 0.2 mL, 0.20 mmol) at 0° C. The mixture was stirred and allowed to warm slowly to RT. The mixture was quenched with MeOH/HCl (2M) (1 mL:0.1 mL) then NH4Cl (sat.) added and the mixture diluted with water and EtOAc (pH of aqueous ˜7). The mixture was extracted into EtOAc and the organics combined and dried with brine then Na2SO4. The solvent was removed to afford 20 mg crude residue. This was dissolved in DCM (2 mL) and applied to a silica column, eluting with EtOAc/heptane, to afford Compound 112 (13 mg).).

Workup

  1. customThe mixture was quenched with MeOH/HCl (2M) (1 mL:0.1 mL)
  2. additionNH4Cl (sat.) added
  3. additionthe mixture diluted with water and EtOAc (pH of aqueous ˜7)
  4. extractionThe mixture was extracted into EtOAc
  5. dry with materialdried with brine
  6. customThe solvent was removed
  7. customto afford 20 mg crude residue
  8. washeluting with EtOAc/heptane

Sources & evidence

ORD record
ord-718d28328c2c4ec89fa8f143b9b4ff9c
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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