Hydrochloric Acid → HCID 22119997, compound

HRID 1274615

Reaction equation

HRID 1274615 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21](O)=[O:22])[C:17]=3[CH:24]=2)[C:3]1=[O:25].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:38][S:39]([NH2:42])(=[O:41])=[O:40].N12CCCN=C1CCCCC2.Cl>O1CCCC1.C(Cl)Cl.C(O)(=O)C>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([NH:42][S:39]([CH3:38])(=[O:41])=[O:40])=[O:22])[C:17]=3[CH:24]=2)[C:3]1=[O:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 111878605-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid

Product 1

HCID 22119997HCID 22119997, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21922555Acetic acid methylene chlorideSolvent

Procedure

A solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid (0.400 g, 1.08 mmol) in tetrahydrofuran is treated with 1,1'-carbonyldiimidazole (0.260 g, 1.58 mmol), stirred at room temperature for 30 minutes, refluxed for 2 hours, cooled to room temperature, treated dropwise with a solution of methanesulfonamide (0.130 g, 1.37 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.230 g, 1.50 mmol), stirred at room temperature for 3 hours, and poured into 0.5 N hydrochloric acid. The resultant aqueous mixture is extracted with methylene chloride. The organic extracts are combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and a methylene chloride/acetic acid solution (10:1) gives the title product as a white solid (0.350 g, 72%, mp 241-243° C.).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled to room temperature
  3. stirringstirred at room temperature for 3 hours
  4. extractionThe resultant aqueous mixture is extracted with methylene chloride
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a residue

Sources & evidence

ORD record
ord-3c35b67a1f5a4363ac9f09f1978e0b75
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Linked notes

Loading…