Triethylamine → HCID 22091454, compound

HRID 2229200Notes

Reaction equation

HRID 2229200 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[CH2:19][NH:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24].C(N(CC)CC)C.[Cl:33][C:34]1[C:42]([O:43][CH2:44][CH2:45][Br:46])=[C:41]([O:47][CH3:48])[CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37].[OH-].[Na+]>ClCCl>[Cl:33][C:34]1[C:42]([O:43][CH2:44][CH2:45][Br:46])=[C:41]([O:47][CH3:48])[CH:40]=[CH:39][C:35]=1[C:36]([N:20]([CH2:19][C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[C:10]=1[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 22091453HCID 22091453, compoundHCID 131723402HCID 131723402, compound

Product 1

HCID 22091454HCID 22091454, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ({3-[(2-methoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl) (3-methylbutyl) amine (1.4 g, 4.2 mmol) in dichloromethane (15 ml) is added triethylamine (0.7 ml, 5 mmol) followed by 2-chloro-3-bromoethoxy-4-methoxybenzoic acid chloride (1.5 g, 4.5 mmol). The reaction mixture is stirred at ambient temperature for 65 h. Aqueous 1 N sodium hydroxide (20 ml) is added and the resulting mixture is extracted with dichloromethane (3×20 ml). The combined organic layers are dried over magnesium sulfate, filtered, and evaporated at reduced pressure. Chromatography on silica gel with ethyl acetate provides 1.7 g (65%)of (2-chloro-3-bromoethoxy-4-methoxyphenyl)-N-({3-[(2-methoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)} methyl)-N-(3- methylbutyl)carboxamide.

Workup

  1. extractionthe resulting mixture is extracted with dichloromethane (3×20 ml)
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-fb93831fe02f4422ab538f5224000dc5
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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