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

HRID 2174243ノート

反応式

HRID 2174243 の反応式
[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

参加物

5

反応物 2

HCID 896503736-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamideHCID 178418255HCID 178418255、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).).

後処理

  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

出典と根拠

ORDレコード
ord-718d28328c2c4ec89fa8f143b9b4ff9c
出典データセット
uspto-grants-2015_06
特許番号
US09060515B2

反応ノート

読み込み中…