Diisopropylethylamine → HCID 86613955, compound

HRID 504045Notes

Reaction equation

HRID 504045 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.[O:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCN(C(C)C)C(C)C>C(O)(=O)C.CN(C=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]([CH:32]3[CH2:33][CH2:34][O:29][CH2:30][CH2:31]3)[CH2:18][CH2:19]1)[C:10](=[O:20])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 86613954HCID 86613954, compound

Product 1

HCID 86613955HCID 86613955, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

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 tetrahydropyran-4-one (24 μmol, 1.2 eq.) and acetic acid (10 μl). MP-sodium triacetoxy borohydride was added further. After this solution was shaken for several minutes, DIEA (30 μl) was added and a reaction was carried out at 60° C. overnight. The resin was removed by filtration and washed with methylene chloride. The solvent was distilled off with nitrogen gas, 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-(tetrahydropyran-4-yl)piperidin-4-yl]methyl-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione in 30% yield.

Workup

  1. customThe resin was removed by filtration
  2. washwashed with methylene chloride
  3. distillationThe solvent was distilled off with nitrogen gas
  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-1ac2926bc88e4e4b9609a0d196bea454
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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