Dimethylformamide → HCID 86613953, compound

HRID 1811453Notes

Reaction equation

HRID 1811453 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[C:10](=[O:20])[CH2:9][CH2:8]2.CN(C=O)C.[CH3:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH:37]=O.C(N(C(C)C)CC)(C)C>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:34][C:35]3[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=3[CH3:37])[CH2:18][CH2:19]1)[C:10](=[O:20])[CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 107222-MethylbenzaldehydeHCID 81531DiisopropylethylamineHCID 86613954HCID 86613954, compound

Product 1

HCID 86613953HCID 86613953, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-(8-methoxy-1-piperidin-4-ylmethyl-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione (20 μmol, 1.0 eq.) was added a DMF (200 μl) solution of 2-methylbenzaldehyde (24 μmol, 1.2 eq) and acetic acid (10 μl). Si-sodium cyanoborohydride was added further thereto. The solution was shaken for several minutes, diisopropylethylamine (30 μl) was added, and a reaction was carried out at room temperature overnight. The resin was removed by filtration and washed with dichloromethane. The solvent was distilled off from the filtrate in a nitrogen gas stream, and the residue was purified by HPLC (UV-trigger, column: CAPCELL PAK C18, UG 120 S-5, 20 mm×50 mm, 0.05% trifluoroacetic acid-H2O, 0.05% trifluoroacetic acid-CH3CN). The structure was confirmed by LC-MS, and freeze-drying was conducted, giving 5-{8-methoxy-1-[1-(2-methylbenzyl)piperidin-4-yl]methyl-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione in 50.5% yield.

Workup

  1. customThe resin was removed by filtration
  2. washwashed with dichloromethane
  3. distillationThe solvent was distilled off from the filtrate in a nitrogen gas stream
  4. customthe residue was purified by HPLC (UV-trigger, column: CAPCELL PAK C18, UG 120 S-5, 20 mm×50 mm, 0.05% trifluoroacetic acid-H2O, 0.05% trifluoroacetic acid-CH3CN)
  5. customfreeze-drying

Sources & evidence

ORD record
ord-a92e1f2521dc4c919b84006251ba6eb3
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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