2,1,3-Benzothiadiazol-5-amine → 2-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1176195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176195
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[C:15]1[C:28](=[O:29])[N:27]([CH3:30])[C:18]2[N:19]=[C:20](S(C)(=O)=O)[N:21]=[CH:22][C:17]=2[CH:16]=1.[N:31]1[S:32][N:33]=[C:34]2[CH:39]=[C:38]([NH2:40])[CH:37]=[CH:36][C:35]=12>CS(C)=O.O.C(OCC)(=O)C>[N:31]1[S:32][N:33]=[C:34]2[CH:39]=[C:38]([NH:40][C:20]3[N:21]=[CH:22][C:17]4[CH:16]=[C:15]([C:9]5[C:8]([Cl:7])=[CH:13][CH:12]=[CH:11][C:10]=5[Cl:14])[C:28](=[O:29])[N:27]([CH3:30])[C:18]=4[N:19]=3)[CH:37]=[CH:36][C:35]=12

Komponenten

7

Edukt 3

HCID 3143132,1,3-Benzothiadiazol-5-amineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 177473222-(2,1,3-benzothiadiazol-5-ylamino)-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

184 mg of potassium tert-butoxide are added in three installments, at ambient temperature under argon, to 300 mg of compound of formula (II), 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, and 170 mg of the compound of formula (III), 2,1,3-benzothiadiazol-5-ylamine, in suspension in 5 ml of DMSO. After a contact time of 30 minutes, the reaction medium is diluted with a mixture of water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are then washed with water and then with a saturated NaCl solution. After drying over Na2SO4 and filtering, the solvent is evaporated and then the residue is taken up in a few milliliters of ethyl acetate. The green precipitate obtained is filtered off and then chromatographed on silica (gradient: DCM 100 to DCM/MeOH 90:10). 105 mg of the expected product are isolated in the solid form.

Aufarbeitung

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washthe combined organic phases are then washed with water
  3. dry with materialAfter drying over Na2SO4
  4. filtrationfiltering
  5. customthe solvent is evaporated
  6. customThe green precipitate obtained
  7. filtrationis filtered off
  8. customchromatographed on silica (gradient: DCM 100 to DCM/MeOH 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-a1c8e0dba20745c980c6a95d442d3d59
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842806B2

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