Triethylamine → [2-Amino-6-(1-ethanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

HRID 30121

Reaktionsgleichung

Reaktionsgleichung von HRID 30121
F[C:2](F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13]N=[C:11]([NH:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[N:10]=1.C(N(CC)CC)C.[CH2:40]([S:42](Cl)(=[O:44])=[O:43])[CH3:41]>C(Cl)Cl>[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13][CH:2]=[C:11]([NH:26][CH:27]2[CH2:28][CH2:29][N:30]([S:42]([CH2:40][CH3:41])(=[O:44])=[O:43])[CH2:31][CH2:32]2)[N:10]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 21070627[4-Amino-2-(piperidin4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt

Produkt 1

HCID 11495806[2-Amino-6-(1-ethanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanoneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt (0.0589 mmol, Example 22) in methylene chloride (1.25 mL) were added triethylamine (0.065 mL, 0.466 mmol, Aldrich) and a solution of ethanesulfonyl chloride (8.1 mg, 0.062 mmol, Aldrich 99+%) in methylene chloride (0.33 mL) at 0° C. After 5 minutes the reaction mixture was allowed to stir at room temperature for 1 hr before it was concentrated in vacuo. The residue was absorbed on silica gel and purified with 99.5/0.5495/5 of methylene chloride/methanol to give [2-amino-6-(1-ethanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (16.0 mg, 63% yield). HRMS, observed: 437.1660, Calcd for (M+H)+: 437.1654.

Aufarbeitung

  1. customat 0° C
  2. concentrationwas concentrated in vacuo
  3. customThe residue was absorbed on silica gel
  4. custompurified with 99.5/0.5495/5 of methylene chloride/methanol

Quellen und Nachweise

ORD-Eintrag
ord-78e62843d93e4c928f66262cd5ff0168
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423051B2

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