Triethylamine → HCID 117701726, compound

HRID 1507435Notes

Reaction equation

HRID 1507435 reaction equation
Cl.[OH:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([CH3:19])=[C:9]([C@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)[O:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.Br[CH2:29][CH2:30][O:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1>CN(C)C=O>[OH:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([CH3:19])=[C:9]([C@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH2:29][CH2:30][O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran2×HCID 117701579HCID 117701579, compound

Product 1

HCID 117701726HCID 117701726, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxy-3,8-dimethyl-2-[(2R)-pyrrolidin-2-yl]-4H-chromen-4-one hydrochloride (70 mg, 0.27 mmol) obtained in Example 2-3 and triethylamine (56 μL, 0.40 mmol) in dimethylformamide (1.5 mL), 2-(2-bromoethoxy)tetrahydro-2H-pyran (163 μL, 1.08 mmol) was added dropwise, and then the mixture was stirred at room temperature for 20 hours. Triethylamine (38 μL, 0.27 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (41 μL, 0.27 mmol) were further added dropwise thereto, and then the mixture was stirred at room temperature for 27 hours. The reaction solution was concentrated, and then the obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→90/10) to obtain 77 mg of the title compound (yield: 74%).

Workup

  1. stirringthe mixture was stirred at room temperature for 27 hours
  2. concentrationThe reaction solution was concentrated
  3. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→90/10)

Sources & evidence

ORD record
ord-22f6cc4c1f494deb84c4640deef23cfc
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

Loading…