Diisopropylethylamine → 1'-(3-Imidazol-1-yl-propyl)-3,3''-dimethyl-1',2',3',4',5',6'-hexahydro-[2,2'; 6',2'']terpyridine

HRID 1987381Notes

Reaction equation

HRID 1987381 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:22][CH2:23][CH2:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.CCN(C(C)C)C(C)C>CN(C=O)C>[N:25]1([CH2:24][CH2:23][CH2:22][N:9]2[CH:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 120386541-(3-Bromopropyl)-1H-imidazoleHCID 674211653,3''-Dimethyl-1',2',3',4',5',6'-hexahydro-[2,2'; 6',2'']terpyridine

Product 1

HCID 674204831'-(3-Imidazol-1-yl-propyl)-3,3''-dimethyl-1',2',3',4',5',6'-hexahydro-[2,2'; 6',2'']terpyridineYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using General Procedure A: 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (91.3 mg, 0.341 mmol), 1-(3-Bromo-propyl)-1H-imidazole (129 mg, 0.680 mmol), KI (5.6 mg, 0.034 mmol), DIPEA (0.18 mL, 1.02 mmol), and DMF (3.4 mL) were stirred at 60° C. overnight. Purification of the crude material by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 90:5:5) followed by radial chromatography on a 1 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 96:2:2) afforded the free base of the title compound (48 mg, 38%) as a colorless oil.

Workup

  1. customPurification of the crude material by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 90:5:5)

Sources & evidence

ORD record
ord-3a2b425c5a754b439325ffcb11cdfe6a
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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