Triethylamine → HCID 178503264, compound

HRID 724280Notes

Reaction equation

HRID 724280 reaction equation
[CH3:1][S:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.S(O)(=O)(=O)C.[CH2:31]([O:38][C:39]([C@H:41]1[CH2:46][CH2:45][C@@H:44]([NH2:47])[CH2:43][CH2:42]1)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH2:31]([O:38][C:39]([C@H:41]1[CH2:46][CH2:45][C@@H:44]([NH:47][C:10]([C:9]2[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:18][CH:17]=3)=[N:16][CH:15]=[CH:14][CH:13]=2)=[O:12])[CH2:43][CH2:42]1)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 218771372-(4-Methylsulfanyl-phenoxy)-nicotinic acidHCID 178505346HCID 178505346, compound

Product 1

HCID 178503264HCID 178503264, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-methylsulfanyl-phenoxy)-nicotinic acid (3.0 g, 11.5 mmol) was dissolved in dimethylformamide (60 ml) and triethylamine (4.8 ml, 34.4 mmol) was added followed by cis-4-Amino-cyclohexanecarboxylic acid benzyl ester mesylate (4.66 g, 11.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.42 g, 12.6 mmol) and 1-hydroxybenzotriazole (1.71 g, 12.6 mmol). The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between sat. sodium bicarbonate solution (50 ml) and ethyl acetate (50 ml) and the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (25 ml), brine (25 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume) to give cis-4-{[2-(4-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexanecarboxylic acid benzyl ester (4.75 g) as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between sat. sodium bicarbonate solution (50 ml) and ethyl acetate (50 ml)
  3. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
  4. washThe combined organic extracts were washed with water (25 ml), brine (25 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume)

Sources & evidence

ORD record
ord-8218a344fcbc4f2ab0acf7a9c3c68c94
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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