Cyclopentylamine → HCID 68284418, compound

HRID 1469510Notes

Reaction equation

HRID 1469510 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.[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1>O>[CH:29]1([NH:34][CH:15]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:14][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:28][CH2:27][C:5]2=3)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 86677141HCID 86677141, compound

Product 1

HCID 68284418HCID 68284418, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Methanesulfonic acid 2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethylester (240 mg, 0.60 mmol) was dissolved in 10 mL of 70% cyclopentylamine solution in water and heated at 100° C. for 18 h. The reaction mixture was cooled to RT and concentrated to obtain the crude product, which was purified by reverse phase chromatography to obtain 11 mg of cyclopentyl-[2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-pyridin-4-yl-ethyl]-amine. 1H NMR (CDCl3, freebase): δ (ppm): 8.51 (d, 2H), 7.17 (m, 4H), 7.003 (d, 1H), 4.16 (m, 2H), 4.05 (dd, 1H), 3.79 (dd, 2H), 2.9 (m, 1H), 2.83 (m, 2H), 2.55 (s, 3H), 2.44 (s, 3H), 2.39 (m, 1H), 1.99 (s, 2H), 1.7 (m, 2H), 1.5 (m, 2H), 1.4 (m, 1H), 1.9 (m, 2H). Chiral HPLC separates the racemate into enantiomers II-9a-b.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated
  3. customto obtain the crude product, which
  4. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-7be323b483964df3a63d7450e621f6a3
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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