Potassium Carbonate → HCID 57595542, compound

HRID 1786071Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][CH2:40][N:41]1[CH:45]=[CH:44][CH:43]=[CH:42]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:39][CH2:40][N:41]4[CH:45]=[CH:44][CH:43]=[CH:42]4)=[CH:27][CH:28]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.11 g, 0.25 mmol) was dissolved in DMF at room temperature and K2CO3 (0.207 g, 1.5 mmol) was added. 1-(2-Bromo-ethyl)-1H-pyrrole (0.088 g, 0.5 mmol) was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (70% EtOAc/30% Hexane) to afford the product (0.114 g, 85%).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was partitioned between ethyl acetate and water
extractionextracted three times with ethyl acetate
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated down
customThe crude residue was purified by silica gel chromatography (70% EtOAc/30% Hexane)

Sources & evidence

ORD record: ord-adc59ff1a427431fadd3ec78bed0fab1
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

Loading…