1-Hydroxybenzotriazole → HCID 178482472, compound

HRID 1620469Notes

Reaction equation

HRID 1620469 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[CH3:42][NH:43][C:44]1=[N:45][C:46](=[O:56])[S:47]/[C:48]/1=[CH:49]\[CH:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C)C=O.O.C(N(CC)CC)C>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:53]1[CH2:54][CH2:55][CH:50](/[CH:49]=[C:48]2/[C:44]([NH:43][CH3:42])=[N:45][C:46](=[O:56])[S:47]/2)[CH2:51][CH2:52]1)=[O:7]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1417522,4-Bis(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482469HCID 178482469, compound

Product 1

HCID 178482472HCID 178482472, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2,4-bis(trifluoromethyl)benzoic acid (83 mg) in N,N-dimethylformamide (6 mL) were added 1-hydroxybenzotriazole (123 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (154 mg), and the mixture was stirred for 5 min under ice-cooling. To the reaction mixture were added triethylamine (0.2 mL) and (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) under ice-cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate/pentane to give the title compound (85 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  9. customrecrystallized from ethyl acetate/pentane

Sources & evidence

ORD record
ord-ace52515df45495d972d3bb4af8b426c
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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