Triethylamine → HCID 19069319, compound

HRID 1957330Notes

Reaction equation

HRID 1957330 reaction equation
[CH:1]1([C:5]([OH:7])=O)[CH2:4][CH2:3][CH2:2]1.Cl.[O:9]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C1COCC1>[O:9]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)=[O:7])=[CH:22][CH:23]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 19494Cyclobutanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222930261-(4-Phenoxyphenyl)methanamine--hydrogen chloride (1/1)

Product 1

HCID 19069319HCID 19069319, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of cyclobutanecarboxylic acid (0.26 g, 2.6 mmol), 4-phenoxybenzylamine hydrochloride (0.62 g, 2.6 mmol), HOBt, (0.71 g, 5.2 mmol) and triethylamine (1.1 mL, 7.83 mmol) in THF (9 mL) was added EDCl (0.55 g, 2.6 mmol). The mixture was stirred for 18 hours at room temperature. The solvent was removed, and the residue was suspended in ether and washed with 0.1N HCl, 5% NaHCO3 and brine. The ether layer was dried (MgSO4), filtered through a plug of silica gel and concentrated in vacuo to provide 0.70 g (96%) of the title compound as a white solid. m.p. 69°-71° C. 1H NMR (CDCl3, 300 MHz) δ1.80-2.06 (m, 2H), 2.10-2.14 (m, 2H), 2.15-2.39 (m, 2H), 3.02 (pd, J=7.5, 1.2 Hz, 1H), 4.41 (d, J=6 Hz, 2H), 5.55 (br s, 1H), 6.94-7.04 (m, 4H), 7.08-7.15 (tt, J=7.5, 1.5 Hz, 1H), 7.20-7.28 (m, 2H), 7.30-7.38 (m, 2H). MS (DCl/NH3) m/e 282 (M+H)+.

Workup

  1. customThe solvent was removed
  2. washwashed with 0.1N HCl, 5% NaHCO3 and brine
  3. dry with materialThe ether layer was dried (MgSO4)
  4. filtrationfiltered through a plug of silica gel
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd9ed25b42894b44ab5c6f43f4791f2f
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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