Benzoic Acid → L-159913

HRID 36244Notes

Reaction equation

HRID 36244 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:22]([C:26]1[N:27]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[S:55](=[O:58])(=[O:57])[NH2:56])=[CH:45][CH:44]=2)[C:28](=[O:41])[N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([F:40])([F:39])[F:38])[N:30]=1)[CH2:23][CH2:24][CH3:25].N12CCCN=C1CCCCC2>C1COCC1>[C:1]([NH:56][S:55]([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=1[C:46]1[CH:47]=[CH:48][C:43]([CH2:42][N:27]2[C:26]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:30][N:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]([F:40])([F:38])[F:39])[C:28]2=[O:41])=[CH:44][CH:45]=1)(=[O:58])=[O:57])(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 103469025-n-Butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 9939191L-159913Yield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

A solution of 145 mg (1.18 mmole) of benzoic acid and 192 mg (1.18 mmole) of 1,1'-carbonyldiimidazole in 1 mL of THF was stirred under N2 at 55° C. for 2 hours. Then a solution of 157 mg (0.296 mmole) of 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step C) and 133 mL (135 mg, 0.888 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 1 mL of THF was added dropwise. After being stirred overnight at 55° C., the mixture was partitioned between ethyl acetate and 5% citric acid (aqueous). The organic layer was washed with H2O and then with saturated NaCl solution. The ethyl acetate phase was then dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography of the residue as in Example 16, Step D, gave 159 mg (85%) of the title compound, homogeneous by TLC in 98:2 CH2Cl2 --MeOH and comparable in physical properties to the product made according to Example 16, Step D.

Workup

  1. customthe mixture was partitioned between ethyl acetate and 5% citric acid (aqueous)
  2. washThe organic layer was washed with H2O
  3. dry with materialThe ethyl acetate phase was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd680c27f2b344c287b1fd4ac9e06369
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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