2,1,3-Benzothiadiazol-5-amine → HCID 86627853, compound

HRID 1176198Notes

Reaction equation

HRID 1176198 reaction equation
CC(C)([O-])C.[K+].C([Si](C)(C)[C:12]#[C:13][CH2:14][N:15]1[C:20]2[N:21]=[C:22](S(C)(=O)=O)[N:23]=[CH:24][C:19]=2[CH:18]=[C:17]([C:29]2[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:36])[C:16]1=[O:37])(C)(C)C.[N:40]1[S:41][N:42]=[C:43]2[CH:48]=[C:47]([NH2:49])[CH:46]=[CH:45][C:44]=12>CS(C)=O.O.C(OCC)(=O)C>[N:40]1[S:41][N:42]=[C:43]2[CH:48]=[C:47]([NH:49][C:22]3[N:23]=[CH:24][C:19]4[CH:18]=[C:17]([C:29]5[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=5[Cl:36])[C:16](=[O:37])[N:15]([CH2:14][C:13]#[CH:12])[C:20]=4[N:21]=3)[CH:46]=[CH:45][C:44]=12

Participants

7

Reactant 3

HCID 3143132,1,3-Benzothiadiazol-5-amineHCID 23665647Potassium tert-butoxideHCID 68774239HCID 68774239, compound

Product 1

HCID 86627853HCID 86627853, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

62 mg of potassium tert-butoxide are added in 3 installments, at ambient temperature under argon, to 180 mg of compound of formula (II), described below, 8-[3-((tert-butyl)dimethylsilanyl)prop-2-ynyl]-6-(2,6-dichlorophenyl)-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one, and 81 mg of the compound of formula (III), 2,1,3-benzothiadiazol-5-ylamine, in solution in 5 ml of DMSO. After a contact time of 75 min, the reaction medium is diluted with a mixture of water and ethyl acetate. The aqueous phase is brought back to neutral pH and extracted with dichloromethane. After drying the organic phase over sodium sulfate and filtering, the residue is chromatographed on silica (gradient: CH2Cl2 100 to CH2Cl2/MeOH 98:2) to give 52 mg of the expected product.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialAfter drying the organic phase over sodium sulfate
  3. filtrationfiltering
  4. customthe residue is chromatographed on silica (gradient: CH2Cl2 100 to CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-47e742af95b84b9b92036a0a5e93f6ba
Source dataset
uspto-grants-2010_11
Patent number
US07842806B2

Reaction notes

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