Hydrochloric Acid → HCID 70100353, compound

HRID 1274576Notes

Reaction equation

HRID 1274576 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]([C:33]4[CH:38]=[C:37]([O:39][CH2:40][C:41]([OH:43])=O)[CH:36]=[CH:35][C:34]=4[CH3:44])[C:29]=3[CH:45]=2)[C:15]1=[O:46].[CH3:47][C:48]1[CH:49]=[CH:50][C:51]([S:54]([NH2:57])(=[O:56])=[O:55])=[CH:52][CH:53]=1.N12CCCN=C1CCCCC2.Cl>O1CCCC1>[CH3:13][N:14]1[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][C:17](=[O:24])[N:16]([C:25]2[CH:26]=[CH:27][C:28]3[S:32][N:31]=[C:30]([C:33]4[CH:38]=[C:37]([O:39][CH2:40][C:41]([NH:57][S:54]([C:51]5[CH:52]=[CH:53][C:48]([CH3:47])=[CH:49][CH:50]=5)(=[O:55])=[O:56])=[O:43])[CH:36]=[CH:35][C:34]=4[CH3:44])[C:29]=3[CH:45]=2)[C:15]1=[O:46]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6269P-ToluenesulfonamideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70099232HCID 70099232, compound

Product 1

HCID 70100353HCID 70100353, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 1,1'-carbonyldiimidazole (0.198 g, 1.22 mmol) and {{2-{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}-p-tolyl}oxy}acetic acid (0.300 g, 0.610 mmol) in tetrahydrofuran is stirred overnight at room temperature, refluxed for 30 minutes, cooled to room temperature, treated sequentially with a solution of p-toluenesulfonamide (0.209 g, 1.22 mmol) in tetrahydrofuran and a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.204 g, 1.34 mmol) in tetrahydrofuran, stirred at room temperature for three hours, and poured into 10% hydrochloric acid. The resulting aqueous mixture is filtered to obtain a solid. The solid is recrystallized from an acetonitrile/water solution to give the title product as an off-white solid (0.200 g, mp 140-144° C.).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperaturecooled to room temperature
  3. filtrationThe resulting aqueous mixture is filtered
  4. customto obtain a solid
  5. customThe solid is recrystallized from an acetonitrile/water solution

Sources & evidence

ORD record
ord-f7085899fd1a484d97da42114347a700
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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