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

HRID 2174243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174243
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-718d28328c2c4ec89fa8f143b9b4ff9c
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09060515B2

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