Hydrochloric Acid → HCID 10048964, compound

HRID 2384312Notes

Reaction equation

HRID 2384312 reaction equation
Cl.CN(C)CCCN=C=NCC.[Br:13][C:14]1[CH:22]=[C:18]([C:19]([OH:21])=O)[C:17]([OH:23])=[CH:16][CH:15]=1.[F:24][C:25]([F:39])([F:38])[C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:29][NH2:30].Cl>CN(C)C1C=CN=CC=1.O1CCCC1>[F:24][C:25]([F:38])([F:39])[C:26]1[CH:27]=[C:28]([CH2:29][NH:30][C:19](=[O:21])[C:18]2[CH:22]=[C:14]([Br:13])[CH:15]=[CH:16][C:17]=2[OH:23])[CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69725-Bromosalicylic acidHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×

Product 1

HCID 10048964HCID 10048964, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (it is abbreviated as WSC.HCl hereafter.; 192 mg, 1 mmol) was added to a mixture of 5-bromosalicylic acid (217 mg, 1 mmol), 3,5-bis(trifluoromethyl)benzylamine (243 mg, 1 mmol), 4-dimethylaminopyridine (12 mg, 0.1 mmol) and tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (244.8 mg, 55.4%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9bc4e79a73a348f19b37f4fa9a3c486f
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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