HCID 60197172, compound → HCID 68283794, compound

HRID 2408700Notes

Reaction equation

HRID 2408700 reaction equation
[CH3:1][N:2]1[CH2:26][CH2:25][C:5]2[N:6]([CH2:14][CH:15]([C:17]3[CH:18]=[N:19][C:20]([O:23]C)=[CH:21][CH:22]=3)[OH:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1>Cl>[CH3:1][N:2]1[CH2:26][CH2:25][C:5]2[N:6]([CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][CH:18]=3)[OH:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

3

Reactant 1

HCID 60197172HCID 60197172, compound

Product 1

HCID 68283794HCID 68283794, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-(6-methoxy-pyridin-3-yl)-ethanol (200 mg, 0.569 mmol) in 3N HCl (8 mL) was stirred at 100° C. for 3 h. The reaction mixture was concentrated under reduced pressure and residue was purified by reverse phase HPLC to yield 5-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-1-hydroxyethyl)pyridin-2(1H)-one. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.5 (m, 1H), 7.23 (s, 1H), 7.2 (s, 1H), 7.19 (d, 1H), 6.5 (s, 1H), 4.62 (d, 1H), 4.19-4.37 (m, 3H), 3.8 (m, 1H), 3.5 (m, 1H), 3.24 (m, 2H), 3.1 (m, 4H), 2.4 (s, 3H). Separation by chiral HPLC provides enantiomers II-92a-b.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and residue
  2. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-cad673fa5c0e4563ac24d31f4e838f06
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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