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

HRID 1176197Notes

Reaction equation

HRID 1176197 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([N:12]2[C:17]3[N:18]=[C:19](S(C)(=O)=O)[N:20]=[CH:21][C:16]=3[CH:15]=[C:14]([C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:33])[C:13]2=[O:34])[CH2:11][CH2:10][CH2:9][CH2:8]1.[N:35]1[S:36][N:37]=[C:38]2[CH:43]=[C:42]([NH2:44])[CH:41]=[CH:40][C:39]=12>CS(C)=O.O.C(OCC)(=O)C>[N:35]1[S:36][N:37]=[C:38]2[CH:43]=[C:42]([NH:44][C:19]3[N:20]=[CH:21][C:16]4[CH:15]=[C:14]([C:26]5[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=5[Cl:33])[C:13](=[O:34])[N:12]([CH:7]5[CH2:11][CH2:10][CH2:9][CH2:8]5)[C:17]=4[N:18]=3)[CH:41]=[CH:40][C:39]=12

Participants

7

Reactant 3

HCID 3143132,1,3-Benzothiadiazol-5-amineHCID 23665647Potassium tert-butoxideHCID 687782018-cyclopentyl-6-(2,6-dichlorophenyl)-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 177473262-(2,1,3-benzothiadiazol-5-ylamino)-8-cyclopentyl-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

202 mg of potassium tert-butoxide are added in 3 installments, at ambient temperature under argon, to 500 mg of compound of formula (II), 8-cyclopentyl-6-(2,6-dichlorophenyl)-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, and 249 mg of the compound of formula (III), 2,1,3-benzothiadiazol-5-ylamine, in suspension in 18 ml of DMSO. After a contact time of 45 min, 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 sodium sulfate and filtering, the residue is chromatographed on silica (gradient: heptane 100 to heptane/ethyl acetate 60:40) and precipitated from diethyl ether to give 283 mg of the expected product in the form of a yellow solid.

Workup

  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 sodium sulfate
  4. filtrationfiltering
  5. customthe residue is chromatographed on silica (gradient: heptane 100 to heptane/ethyl acetate 60:40)
  6. customprecipitated from diethyl ether

Sources & evidence

ORD record
ord-4388768ad08048a1ba9bf0df2664539f
Source dataset
uspto-grants-2010_11
Patent number
US07842806B2

Reaction notes

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