Ethylamine → HCID 68284354, compound

HRID 1469509Notes

Reaction equation

HRID 1469509 reaction equation
[CH3:1][N:2]1[CH2:28][CH2:27][C:5]2[N:6]([CH2:14][CH:15](OS(C)(=O)=O)[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH2:29]([NH2:31])[CH3:30]>O>[CH3:1][N:2]1[CH2:28][CH2:27][C:5]2[N:6]([CH2:14][CH:15]([NH:31][CH2:29][CH3:30])[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 86677141HCID 86677141, compound

Product 1

HCID 68284354HCID 68284354, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonicacid-2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethylester (300 mg, 0.75 mmol) in 70% ethylamine in water (15 mL) was heated at 100° C. for 18 h. The reaction mixture was cooled to RT and extracted with EtOAc (2×100 mL). The combined organic layer was washed with water (2×20 mL), dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by reverse phase chromatography to obtain 55 mg of [2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethyl]-ethyl-amine. 1H NMR (DMSO, TFA salt): δ (ppm): 8.5 (d, 2H), 7.3 (d, 1H), 7.2 (m, 3H), 6.9 (d, 1H), 4.7 (m, 2H), 4.43 (m, 2H), 4.1 (d, 1H), 3.3 (m, 1H), 3.0 (m, 2H), 2.85 (d, 6H), 2.8 (m, 1H), 2.5 (m, 2H), 2.3 (s, 3H), 1.22 (s, 3H). Chiral HPLC separates the racemate into enantiomers II-8a-b.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washThe combined organic layer was washed with water (2×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto obtain the crude product, which
  6. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-ffe34d6e1c7c44d5a89a6d6eaf1614ea
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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