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 1753177노트

반응식

HRID 1753177 반응식
[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

참가 물질

6

반응물 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

생성물 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-one수율 39%

시약·촉매·용매 3

HCID 62662Ferrous sulfate heptahydrate촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0dceadee34ec46ba88e7f1d2b6977a61
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163029B2

반응 노트

불러오는 중…