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Sodium hydride → N-[6-Chloro-2-[(3-chloro-2-fluorobenzyl)thio]-4-pyrimidinyl]-4-methyl-1-piperazinesulfonamide

HRID 729666
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Reaktionsgleichung

Reaktionsgleichung von HRID 729666
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[C:17]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[F:31])[N:16]=1>CN(C=O)C>[Cl:14][C:15]1[N:16]=[C:17]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[F:31])[N:18]=[C:19]([NH:11][S:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)(=[O:10])=[O:9])[CH:20]=1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 143260054-Methylpiperazine-1-sulfonamideHCID 859280174,6-Dichloro-2-[(3-chloro-2-fluorobenzyl)thio]pyrimidine

Produkt 1

HCID 86602819N-[6-Chloro-2-[(3-chloro-2-fluorobenzyl)thio]-4-pyrimidinyl]-4-methyl-1-piperazinesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

To a solution of the subtitle product of step i) (2.0 g) in dry DMF (20 ml) at 0° C. was added 60% sodium hydride (0.9 g) portionwise over 5 min. After further stirring at 0° C. for 30 min the subtitle product from step iii) (3.6 g) in DMF (10 ml) was added and the whole allowed to stir at room temperature for 24 h. The reaction mixture was carefully quenched with aqueous 2M hydrochloric acid until pH 7.4. The solvent was evaporated to dryness and the residue dissolved in a mixture of methanol/EtOAc and applied to an SCX column followed by further elution with EtOAc. This was then followed by elution with EtOAc/triethylamine mixtures and these fractions evaporated to dryness. The subtitle compound was obtained pure by trituration with Et2O and filtration, leaving a white solid. Yield: 1.5 g.

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was carefully quenched with aqueous 2M hydrochloric acid until pH 7.4
  3. customThe solvent was evaporated to dryness
  4. dissolutionthe residue dissolved in a mixture of methanol/EtOAc
  5. washfollowed by further elution with EtOAc
  6. washThis was then followed by elution with EtOAc/triethylamine mixtures
  7. customthese fractions evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b3d769ac89024d43b19891d2e3ce0af0
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07582644B2

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