Triethylamine → HCID 66674828, compound

HRID 1879308Notes

Reaction equation

HRID 1879308 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-6f534630138c4062bb67a4932e79ea92
Source dataset
uspto-grants-2012_11
Patent number
US08314128B2

Reaction notes

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