Hydrochloric Acid → HCID 22119899, compound

HRID 1274652Notes

Reaction equation

HRID 1274652 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][N:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17](=[O:24])[N:16]([C:25]2[CH:26]=[CH:27][C:28]3[S:32][N:31]=[C:30]([CH2:33][O:34][CH2:35][C:36](O)=[O:37])[C:29]=3[CH:39]=2)[C:15]1=[O:40].[CH3:41][S:42]([NH2:45])(=[O:44])=[O:43].N12CCCN=C1CCCCC2.Cl>O1CCCC1>[CH3:13][N:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17](=[O:24])[N:16]([C:25]2[CH:26]=[CH:27][C:28]3[S:32][N:31]=[C:30]([CH2:33][O:34][CH2:35][C:36]([NH:45][S:42]([CH3:41])(=[O:44])=[O:43])=[O:37])[C:29]=3[CH:39]=2)[C:15]1=[O:40]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53768367HCID 53768367, compound

Product 1

HCID 22119899HCID 22119899, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyldiimidazole (1.17 g, 0.00722 mol) is added to a solution of {{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}methoxy}acetic acid (1.50 g, 0.00361 mol) in tetrahydrofuran. The mixture is stirred one hour at reflux and cooled to room temperature. Methylsulfonamide (0.755 g, 0.00794 mol) is added, followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.19 ml, 0.00794 mol). The resultant mixture is stirred overnight at room temperature, poured into 10% hydrochloric acid, and filtered. The resultant white solid is triturated in tetrahydrofuran, and filtered to give the title compound as an off-white solid (1.00 g, 56.2%, mp >240° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. customThe resultant white solid is triturated in tetrahydrofuran
  4. filtrationfiltered

Sources & evidence

ORD record
ord-753350da7d4f4c1dbe32c159143bfeea
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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