Chloroacetyl chloride → 2-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamide

HRID 1668401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668401
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][NH:29][CH3:30])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.[Cl:31][CH2:32][C:33](Cl)=[O:34].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[Cl:31][CH2:32][C:33]([N:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][N:15]2[C:16](=[O:19])[C:17]3[S:18][C:10]([C:7]4[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=4)=[CH:11][C:12]=3[N:13]=[CH:14]2)=[CH:23][CH:24]=1)[CH3:30])=[O:34]

Komponenten

6

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

Produkt 1

HCID 592398302-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamideAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of the compound (200 mg) obtained in Example 4, chloroacetyl chloride (51 mg), triethylamine (146 mg) and tetrahydrofuran (2 ml) was stirred at 60° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (20:1, volume ratio)] and crystallized from hexane to give the title compound (130 mg) as a colorless powder.

Aufarbeitung

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (20:1, volume ratio)]
  5. customcrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-5ad54534f75d4252ba8ceea86b15a4f9
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989445B2

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