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Methanol → 1-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]piperazine-2,6-dione

HRID 459774
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HRID 459774 반응식
C([O-])=O.[NH4+].C([N:12]1[CH2:17][C:16](=[O:18])[N:15]([C:19]2[CH:24]=[C:23]([CH2:25][C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29](=[O:36])[NH:28][N:27]=3)[CH:22]=[CH:21][C:20]=2[F:37])[C:14](=[O:38])[CH2:13]1)C1C=CC=CC=1.CO>O.[Pd]>[F:37][C:20]1[CH:21]=[CH:22][C:23]([CH2:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29](=[O:36])[NH:28][N:27]=2)=[CH:24][C:19]=1[N:15]1[C:14](=[O:38])[CH2:13][NH:12][CH2:17][C:16]1=[O:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 184443764-Benzyl-1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]piperazine-2,6-dione

생성물 1

HCID 184443391-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]piperazine-2,6-dione

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 962
Water
용매

실험 절차

A solution of ammonium formate (0.55 g, 8.8 mmol) in water (5 ml) was added to a stirred mixture of 4-benzyl-1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]piperazine-2,6-dione (1 g, 2.2 mmol; prepared in a manner similar to that described in Example 31), 10% palladium on carbon catalyst (0.33 g) and methanol (15 ml), the mixture was heated under reflux for 1 hour, then it was cooled to ambient temperature and filtered through a pad of Celite filter aid. The filter pad was washed with methanol (50 ml), then the combined filtrate and washings were concentrated in vacuo. The residue was diluted with water (20 ml), the product was extracted into ethyl acetate (4×20 ml), the combined extracts were dried (MgSO4) and the solvent was removed in vacuo to give 1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]piperazine-2,6-dione (0.8 g) as a pale brown solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 3.3 (2× overlapping d, 4H) (2×ring CH2), 4.25 (s, 2H) (ArCH2—), 6.95–7.2 (m, 2H) (2×ArH), 7.7–7.9 (m, 3H) (3×ArH), 7.95 (d, 1H) (ArH), 8.2 (d, 1H) (ArH), 9.7 (s, 1H) (piperazine NH), 12.6 (s, 1H) (CONH).

후처리

  1. customprepared in a manner similar to
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. filtrationfiltered through a pad of Celite
  5. filtrationfilter aid
  6. washThe filter pad was washed with methanol (50 ml)
  7. concentrationthe combined filtrate and washings were concentrated in vacuo
  8. additionThe residue was diluted with water (20 ml)
  9. extractionthe product was extracted into ethyl acetate (4×20 ml)
  10. dry with materialthe combined extracts were dried (MgSO4)
  11. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-dff40e71dbfa45b884a3263e0d6d0ff9
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07196085B2

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