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

HRID 459774
ノート
印刷プレビュー

反応式

HRID 459774 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 962
Water
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dff40e71dbfa45b884a3263e0d6d0ff9
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07196085B2

反応ノート

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