Ammonium formate → 3-[3-[[1-(2-Hydroxyphenyl)-1-methylethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester

HRID 1697333ノート

反応式

HRID 1697333 の反応式
Br[C:2]1[N:3]=[C:4]([NH:20][C:21]([CH3:37])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29]CC2C=CC=CC=2)[CH3:22])[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11]([O:13][CH3:14])=[O:12])[CH:7]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:8]([N:6]2[CH:7]=[CH:2][N:3]=[C:4]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[OH:29])([CH3:37])[CH3:22])[C:5]2=[O:19])[CH:9]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 666898163-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester

生成物 1

HCID 666901483-[3-[[1-(2-Hydroxyphenyl)-1-methylethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester収率 100.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

To 3-[5-bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester (Example 220a, 2 g) in ethanol (50 mL) was added ammonium formate (3.14 g) and 10% Pd/C (0.378 g) and the reaction heated at 75° C. for 1 h. The reaction was filtered through celite and the filtrate concentrated in vacuo. The reaction mixture was diluted with water (250 mL) and extracted with dichloromethane (250 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the subtitle compound (1.410 g).

後処理

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe reaction mixture was diluted with water (250 mL)
  4. extractionextracted with dichloromethane (250 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eeaef9f8edca4dfa8643586b8ffa479a
出典データセット
uspto-grants-2012_04
特許番号
US08163905B2

反応ノート

読み込み中…