Triethylamine → 4-({[2-(3-Nitro-phenoxy)-pyridine-3-carbonyl]-amino}-methyl)-cyclohexanecarboxylic acid ethyl ester

HRID 844066Notes

Reaction equation

HRID 844066 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9][CH2:8]1)=[O:6])[CH3:3].[N+:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[O:21][C:22]1[N:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25])([O-:17])=[O:16].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C.C(N(CC)CC)C>CN(C)C=O.O>[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:24]([C:23]2[C:22]([O:21][C:20]3[CH:31]=[CH:32][CH:33]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=3)=[N:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 13145623Rac-ethyl (1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylate hydrochlorideHCID 21883477Ethylcarbodiimide hydrochlorideHCID 226123442-(3-Nitro-phenoxy)-nicotinic acid

Product 1

HCID 539235484-({[2-(3-Nitro-phenoxy)-pyridine-3-carbonyl]-amino}-methyl)-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-Aminomethyl-cyclohexanecarboxylic acid ethyl ester hydrochloride (0.500 grams, 2.26 mmole), 2-(3-Nitro-phenoxy)-nicotinic acid (0.588 grams, 2.26 mmole), 1-hydroxybenzotriazole hydrate (0.366 grams, 2.71 mmole) and 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.564 grams, 2.93 mmole) in dimethylformamide (50 ml) was was added triethyl amine (0.456 grams, 4.52 mmole) and stirred over the weekend at room temperature. The mixture was diluted with water (150 ml) and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give an oil which was purified by chromatography on silica eluting with 40% ethyl acetate/hexane to give an oil. (1.05 g). MS (m/e) 428 (M++1); 1H NMR (CDCl3) d 1.01 (2H, m), 1.2 (3H, t), 1.4 (2H, q), 1.6 (1H, m), 1.90 (2H, d, J=12.5 Hz), 2.0 (1H, d, J=12.5 Hz), 2.2 (1H, m), 3.4 (2H, m), 4.10 (2H, q), 7.20-8.7 (7H, m).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified by chromatography on silica eluting with 40% ethyl acetate/hexane
  8. customto give an oil

Sources & evidence

ORD record
ord-172ee0bd15fe4c30a1bdd399755a250e
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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