Triethylamine → HCID 66792790, compound

HRID 535001Notes

Reaction equation

HRID 535001 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:6])([CH3:5])[CH3:4].[OH:20][C:21]1[CH:22]=[CH:23][C:24]([C:27](O)=[O:28])=[N:25][CH:26]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:3]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][N:17]([C:27]([C:24]2[N:25]=[CH:26][C:21]([OH:20])=[CH:22][CH:23]=2)=[O:28])[CH2:16][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 66750915HCID 66750915, compound

Product 1

HCID 66792790HCID 66792790, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butyl-4-chlorophenyl)piperazine dihydrochloride (Reference Example 20, 0.50 g, 1.54 mmol), 5-hydroxypyridine-2-carboxylic acid (0.26 g, 1.84 mmol), triethylamine (644 μL, 4.62 mmol), EDCI (0.29 g, 1.84 mmol) and HOBt (0.28 g, 1.84 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 5 days. The reaction mixture was added to saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution, brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 50:50 to 0:100) to give the title compound (0.30 g, 52%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated NaHCO3 solution, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 50:50 to 0:100)

Sources & evidence

ORD record
ord-00bcd36286574ec6a0ce0426dd4ed4f3
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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