2-Amino-3-chloropyridine → N-(3-chloropyridin-2-yl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 627927

Reaktionsgleichung

Reaktionsgleichung von HRID 627927
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][Si](C)(C)N[Si](C)(C)C.[Na].[S:19]1[C:23]2[C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[O:26][CH2:27][CH2:28][C:22]=2[CH:21]=[C:20]1[C:33](Cl)=[O:34]>C1COCC1>[Cl:8][C:7]1[C:2]([N:1]([CH3:9])[C:33]([C:20]2[S:19][C:23]3[C:24]4[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=4[O:26][CH2:27][CH2:28][C:22]=3[CH:21]=2)=[O:34])=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 6932672-Amino-3-chloropyridineHCID 45051731Sodium hexamethyidisilazaneHCID 579001474,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride

Produkt 1

HCID 57900248N-(3-chloropyridin-2-yl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

An ice water cooled solution of 2-amino-3-chloropyridine (0.200 g, 0.755 mmol) in tetrahydrofuran (1.5 mL, 18 mmol) was reacted with a THF solution of 1 M sodium hexamethyldisilazane to give a clear solution. This reaction mix was stirred at cooled temperature for 30 minutes. Next, 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride (0.100 g, 0.378 mmol) was added portionwise as a solid. Reaction mix was stirred at room temperature with monitor for formation of desired product and concentrated in vacuo to a solid residue. This residue was taken into ethyl acetate and the organic was washed with water, then saline and dried (Na2SO4). The crude material was purified by MPLC on silica, eluting with 10% to 80% ethyl acetate/hexanes to give 128 mg N-(3-chloropyridin-2-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide, 34% of theoretical yield.

Aufarbeitung

  1. customto give a clear solution
  2. additionThis reaction mix
  3. temperatureat cooled temperature for 30 minutes
  4. customReaction
  5. additionmix

Quellen und Nachweise

ORD-Eintrag
ord-7e28a68fe7244ece89ccb3be79949963
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309265B2

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