Triethylamine → HCID 66674828, compound

HRID 455897Notes

Reaction equation

HRID 455897 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]([CH3:14])([CH3:13])[C:11]2[CH:10]=[C:9]([C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][C:6]=2[CH2:5][C@H:4]1[O:18][CH3:19].C(N(CC)CC)C.[CH2:27]([O:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH3:28]>>[CH2:27]([O:29][C:30](=[O:33])[CH2:31][CH2:32][NH:2][C@H:3]1[C@H:4]([O:18][CH3:19])[CH2:5][C:6]2[C:11](=[CH:10][C:9]([C:15](=[O:16])[NH2:17])=[CH:8][CH:7]=2)[C:12]1([CH3:14])[CH3:13])[CH3:28]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl Acrylate2×HCID 66674619HCID 66674619, compound

Product 1

HCID 66674828HCID 66674828, compound

Conditions

Temperature
70 °C

Procedure

A mixture of trans-7-amino-6-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide hydrochloride (0.25 g, 0.88 mmol) anhydrous ethanol (0.90 mL), triethylamine (0.14 mL, 1.32 mmol) and acrylic acid ethyl ester (0.14 mL, 1.0 mmol) were heated at 70° C. After 23 h, additional acrylic acid ethyl ester (0.04 mL, 0.3 mmol) was added and heating was continued. Five hours after the addition, the reaction was cooled to room temperature, combined with another run (0.36 mmol scale) and concentrated under vacuum. The title compound (0.61 g) was used without further purification. (m/z): [M+H]+ calcd for C19H28N2O4 349.21. Found 349.0.

Workup

  1. temperatureheating
  2. additionFive hours after the addition
  3. temperaturethe reaction was cooled to room temperature
  4. concentrationconcentrated under vacuum
  5. customThe title compound (0.61 g) was used without further purification

Sources & evidence

ORD record
ord-b8e3e33a11da4e849c34151653089c2e
Source dataset
uspto-grants-2013_07
Patent number
US08497287B2

Reaction notes

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