Triethylamine → 2-[(2-{[4-(3,4-Dichlorophenoxy)piperidin-1-yl]methyl}morpholin-4-yl)carbonyl]6-fluoroimidazo[1,2-a]pyridine

HRID 1292758Notes

Reaction equation

HRID 1292758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)[CH2:8][CH2:7]1.C(N(CC)CC)C.[F:30][C:31]1[CH:32]=[CH:33][C:34]2[N:35]([CH:37]=[C:38]([C:40](Cl)=[O:41])[N:39]=2)[CH:36]=1.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15]([C:40]([C:38]3[N:39]=[C:34]4[CH:33]=[CH:32][C:31]([F:30])=[CH:36][N:35]4[CH:37]=3)=[O:41])[CH2:14]2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 113599152-{[4-(3,4-Dichlorophenoxy)piperidin-1-yl]methyl}morpholineHCID 179747796-Fluoroimidazo[1,2-a]pyridine-2-carbonyl Chloride

Product 1

HCID 101421172-[(2-{[4-(3,4-Dichlorophenoxy)piperidin-1-yl]methyl}morpholin-4-yl)carbonyl]6-fluoroimidazo[1,2-a]pyridineYield 8.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 2, Step (c) (0.2 g) was dissolved in dichloromethane (4 ml) and triethylamine (0.16 ml) added. The product of Step (c) (0.12 g) was then added and the reaction stirred for 2 hrs. Saturated aqueous NaHCO3 solution was added and the product was extracted with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated. Purification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH3(aq) (0.1%) to 95% MeCN/NH3(aq) (0.1%)) gave the title compound (0.024 g).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried with MgSO4
  3. concentrationconcentrated
  4. customPurification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH3(aq) (0.1%) to 95% MeCN/NH3(aq) (0.1%))

Sources & evidence

ORD record
ord-7fe31553f83a4f89b8ed7add2a165b90
Source dataset
uspto-grants-2007_07
Patent number
US07238691B2

Reaction notes

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