Dicyclohexylcarbodiimide → HCID 15022942, compound

HRID 893521Notes

Reaction equation

HRID 893521 reaction equation
[Cl:1][CH:2]([CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]2)[C:10]([Cl:23])=[CH:9][C:8]=1[Cl:24])[C:3]([OH:5])=O.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH:25]1([NH:28][C:3](=[O:5])[CH:2]([Cl:1])[CH2:6][C:7]2[CH:12]=[C:11]([N:13]3[C:17](=[O:18])[N:16]([CH:19]([F:20])[F:21])[C:15]([CH3:22])=[N:14]3)[C:10]([Cl:23])=[CH:9][C:8]=2[Cl:24])[CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 15022941HCID 15022941, compound2×

Product 1

HCID 15022942HCID 15022942, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 0.50 g (0.0013 mole) of 2-chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionic acid (Compound 2), 0.071 g (0.0013 mole) of cyclopropylamine, 0.17 g (0.0013 mole) of 1-hydroxybenzotriazole hydrate, and 0.18 g (0.0014 mole) of N,N-diisopropylethylamine in approximately 15 mL of tetrahydrofuran was cooled to 0° C. To this cold mixture was added 0.26 g (0.0013 mole) of 1,3-dicyclohexylcarbodiimide. After complete addition, the reaction mixture was allowed to warm to room temperature and was stirred for approximately 18 hours. The reaction mixture was filtered. The filtrate was diluted with carbon tetrachloride and was washed in succession with a IN hydrochloric acid solution, an aqueous 10% sodium hydroxide solution, water, and an aqueous saturated sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure to give 0.43 g of N-cyclopropyl2 -chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionamide as a solid, m.p. 139°-143° C., Compound 17 of Table 1.

Workup

  1. additionAfter complete addition
  2. filtrationThe reaction mixture was filtered
  3. additionThe filtrate was diluted with carbon tetrachloride
  4. washwas washed in succession with a IN hydrochloric acid solution
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1fbd9a5e4b284dacabcc8d7ce34fa79e
Source dataset
uspto-grants-1992_06
Patent number
US05125958

Reaction notes

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