Triethylamine → HCID 69694260, compound

HRID 489904Notes

Reaction equation

HRID 489904 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:7]1)=[O:5])[CH3:2].[Cl:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[C:26]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[CH:25]=[C:24]2[C:38](O)=[O:39].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[OH-].[Na+]>ClCCl>[CH2:18]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:13][CH2:14][N:15]([C:38]([C:24]3[C:23]4[C:28](=[CH:29][CH:30]=[C:21]([Cl:20])[CH:22]=4)[N:27]=[C:26]([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)[CH:25]=3)=[O:39])[CH2:16][CH2:17]2)[CH2:7]1)=[O:5])[CH3:19]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 6291016-Chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23150735HCID 23150735, compound

Product 1

HCID 69694260HCID 69694260, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1,4′]bipiperidinyl-3-carboxylic acid diethylamide (0.38 mmol, 115 mg) and 6-chloro-2-(4-chloro-phenyl)-quinoline-4-carboxylic acid (0.417 mmol, 133 mg) in anhydrous dichloromethane was added 1-hydroxybenzotriazole hydrate (0.42 mmol, 56 mg) followed by triethylamine (1.52 mmol, 0.8 mL) then 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.46 mmol, 87 mg). The solution was stirred at ambient temperature for 16 hr then 2M sodium hydroxide (25 mL) was added. The aqueous layer was separated and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. The residue was chromatographed on a silica gel rotor eluting with a 1 to 5% methanol in dichloromethane gradient to give the title compound (63 mg, 29%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under vacuum
  6. customThe residue was chromatographed on a silica gel rotor
  7. washeluting with a 1 to 5% methanol in dichloromethane gradient

Sources & evidence

ORD record
ord-088d8815089e43daa81eb61ef9407fe0
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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