Hydrochloric Acid → HCID 10048964, compound

HRID 421009Notes

Reaction equation

HRID 421009 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-7fc2a8e679db40c8861dbd4a6b4e9911
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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