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Dimethylformamide → Ethyl 2-[(2-bromophenyl)methyl]-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate

HRID 2046281
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2046281
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([OH:21])[C:11]([CH:22]([CH3:24])[CH3:23])=[N:10]1.OC1C(C(C)C)=NNC(=O)[C:27]=1[C:36]([O:38]CC)=[O:37].[H-].[Na+].BrC1C=CC=CC=1CBr.C[N:53](C)C=O>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16]([NH:53][CH2:27][C:36]([OH:38])=[O:37])=[O:17])=[C:12]([OH:21])[C:11]([CH:22]([CH3:24])[CH3:23])=[N:10]1.[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([OH:21])[C:11]([CH:22]([CH3:23])[CH3:24])=[N:10]1
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Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 68813242Ethyl 2-[(2-bromophenyl)methyl]-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylateHCID 68815345Ethyl 5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate

Produkt 2

HCID 54739212
N-{[2-[(2-Bromophenyl)methyl]-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinyl]carbonyl}glycine
HCID 68813242Ethyl 2-[(2-bromophenyl)methyl]-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylateAusbeute 22,32 %

Versuchsvorschrift

Ethyl 2-[(2-bromophenyl)methyl]-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. To a solution of ethyl 5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate (example 46(a), 3 g, 13.26 mmol) in N,N-Dimethylformamide (DMF) (50 ml) at 0° C. was added sodium hydride (0.796 g, 19.89 mmol) in portions. The reaction mixture was stirred at room temperature for 45 minutes and then cooled back to 0° C. and 2-bromobenzylbromide (3.31 g, 13.26) was added portionwise. The mixture was stirred at ambient temperature for 2.5 hours then quenched with 1N HCl (10 ml) and diluted with water (30 ml). The aqueous solution was extracted with ethyl acetate (2×100 ml), the organic layers combined and washed with water (100 ml) and brine (100 ml), dried over Magnesium sulfate, filtered and solvents removed with rotary evaporation. The crude solid was triturated with ether and filtered. The solid material was 100% starting material (1 g). The filtrate was purified by flash column chromatography (10-100% ethyl acetate in hexanes) to provide the title compound (ethyl 2-[(2-bromophenyl)methyl]-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate (1.3 g, 2.96 mmol, 22.32% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) d ppm 12.33 (br. s., 1H), 7.66 (dd, J=8.08, 1.26 Hz, 1H), 7.35 (td, J=7.52, 1.14 Hz, 1H), 7.25 (td, J=7.58, 1.77 Hz, 1H), 7.03 (dd, J=7.83, 1.52 Hz, 1H), 5.20 (s, 2H), 4.28 (q, J=7.07 Hz, 2H), 3.15 (sept, J=6.82 Hz, 1H), 1.26 (t, J=7.07 Hz, 3H), 1.11 (d, J=6.82 Hz, 6 H). MS (ES+) m/e 396 [M+H]+.

Aufarbeitung

  1. temperaturecooled back to 0° C.
  2. stirringThe mixture was stirred at ambient temperature for 2.5 hours
  3. customthen quenched with 1N HCl (10 ml)
  4. additiondiluted with water (30 ml)
  5. extractionThe aqueous solution was extracted with ethyl acetate (2×100 ml)
  6. washwashed with water (100 ml) and brine (100 ml)
  7. dry with materialdried over Magnesium sulfate
  8. filtrationfiltered
  9. customsolvents removed with rotary evaporation
  10. customThe crude solid was triturated with ether
  11. filtrationfiltered
  12. customThe filtrate was purified by flash column chromatography (10-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-263e83b20a3a4624a4a8e35a09d5f382
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE044613E1

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