Ammonium Hydroxide → 7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one

HRID 1753177ノート

反応式

HRID 1753177 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[N:24]([C:25]([C:27]4[C:28]([CH3:32])=[N:29][O:30][CH:31]=4)=[O:26])[CH2:23][CH2:22][N:10]2[C:11](=[O:21])[C:12]2[N:13]([CH:15]=[C:16]([N+:18]([O-])=O)[CH:17]=2)[CH2:14]3)=[CH:5][CH:4]=1.[OH-].[NH4+]>CO.O.S([O-])([O-])(=O)=O.O.O.O.O.O.O.O.[Fe+2]>[NH2:18][C:16]1[CH:17]=[C:12]2[C:11](=[O:21])[N:10]3[CH2:22][CH2:23][N:24]([C:25]([C:27]4[C:28]([CH3:32])=[N:29][O:30][CH:31]=4)=[O:26])[C:9]3([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:14][N:13]2[CH:15]=1

参加物

6

反応物 2

HCID 14923Ammonium HydroxideHCID 5337344110a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-nitro-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

生成物 1

HCID 533733037-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one収率 39%

試薬・触媒・溶媒 3

HCID 62662Ferrous sulfate heptahydrate触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a solution of 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-nitro-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (107 mg, 0.24 mmol) in MeOH (2.4 mL) was added Iron(II) heptahydrate sulfate (544 mg, 2 mmol) in water (2.4 mL). A solution of ammonium hydroxide (28%, 0.7 mL) was added and the mixture was heated at 50° C. for 45 min. The reaction mixture was then partially concentrated in vacuo (half volume), neutralized with a saturated aqueous solution of NH4Cl and then extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtrated and concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4 gradient 0-7% MeOH in EtOAc) to give 7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (111) (38 mg, yield 39%).

後処理

  1. concentrationThe reaction mixture was then partially concentrated in vacuo (half volume)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customto give a residue that
  7. customwas purified by flash chromatography (Biotage SP4 gradient 0-7% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-0dceadee34ec46ba88e7f1d2b6977a61
出典データセット
uspto-grants-2015_10
特許番号
US09163029B2

反応ノート

読み込み中…