1-Hydroxybenzotriazole → HCID 178456943, compound

HRID 1620687Notes

Reaction equation

HRID 1620687 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.ON1[C:23]2C=CC=C[C:22]=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=O)C.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][CH2:42][C:22]#[CH:23])=[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 178456943HCID 178456943, compoundYield 74.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2,4-Bis(trifluoromethyl)benzoic acid (1.20 g) was added to a solution of 1-hydroxybenzotriazole (0.76 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.07 g), (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (1.5 g), triethylamine (1.3 mL) in DMF (50 mL), 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 water and 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/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (1.7 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-42eee78d5a0540d49c6424370d068309
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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