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Trimethylpyruvic acid → 1-(4-(2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-3,3-dimethylbutane-1,2-dione

HRID 1466746
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1466746
OC(C(F)(F)F)=O.[F:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[NH:16][N:15]=2)=[CH:11][C:10]=1[C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28].[CH3:35][C:36]([CH3:43])([CH3:42])[C:37](=[O:41])[C:38](O)=[O:39].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[NH:16][N:15]=2)=[CH:11][C:10]=1[C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:38](=[O:39])[C:37](=[O:41])[C:36]([CH3:43])([CH3:42])[CH3:35])[CH2:31][CH2:30]1)=[O:28]
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Komponenten

6

Edukt 4

HCID 13150Trimethylpyruvic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 865830904-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one 2,2,2-trifluoroacetate

Produkt 1

HCID 57344120
1-(4-(2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-3,3-dimethylbutane-1,2-dione
Ausbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one TFA salt (310 mg, 0.65 mmol), 3,3-dimethyl-2-oxobutanoic acid [1.37 g (60%), 6.3 mmol], DIPEA (2 ml, 11.6 mmol), and HATU (1030 mg, 2.72 mmol) were mixed in DMF (50 ml), the resulting reaction mixture was stirred at room temperature for 44 h until the reaction finished (monitored by TLC). The reaction mixture was then partitioned between DCM and water (100 ml each, the water phase was extracted with DCM (100 ml). The combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was firstly purified by column chromatography on silica gel (DCM:MeOH=100:1) and re-purified by preparative TLC (DCM:MeOH=40:1) to afford the desired product (150 mg, 46.9%) as a off white solid.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was then partitioned between DCM and water (100 ml each
  3. extractionthe water phase was extracted with DCM (100 ml)
  4. washThe combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield the crude product
  9. customThen the crude product was firstly purified by column chromatography on silica gel (DCM:MeOH=100:1)
  10. customre-purified by preparative TLC (DCM:MeOH=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-ccbf0a5e0967483ead37f9c0e568b1b8
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999985B2

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