Tetrahydrofuran → 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide L-(+)-tartrate

HRID 495010Notes

Reaction equation

HRID 495010 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:35])([CH3:34])[O:10]2)=[CH:5][CH:4]=1.O1CCCC1.[C:42]([OH:51])(=[O:50])[C@@H:43]([C@H:45]([C:47]([OH:49])=[O:48])[OH:46])[OH:44]>C(OCC)C>[C:47]([C@@H:45]([C@H:43]([C:42]([OH:51])=[O:50])[OH:44])[OH:46])([OH:49])=[O:48].[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:34])([CH3:35])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 444305L-Tartaric acidHCID 11677552E-2110 free base

Product 1

HCID 866016071-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide L-(+)-tartrateYield 84.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-{1-[2-(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide (100 mg) was dissolved in a mixed solvent consisting of tetrahydrofuran (1 ml) and diethyl ether (25 ml). Thereafter, a mixed solvent consisting of tetrahydrofuran (1 ml) and diethyl ether (25 ml) containing L-(+)-tartaric acid (31 mg) was added to the reaction solution at room temperature. The deposited solid was collected by filtration, and the obtained product was then washed with diethyl ether, so as to obtain the subject compound (110 mg).

Workup

  1. additionwas added to the reaction solution at room temperature
  2. filtrationThe deposited solid was collected by filtration
  3. washthe obtained product was then washed with diethyl ether

Sources & evidence

ORD record
ord-6da6a0d92e6849b8bdd44d6806ab5369
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

Loading…