Triethylamine → N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}morpholine-4-carboxamide

HRID 1070787

Reaction equation

HRID 1070787 reaction equation
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:23]2[CH:22]=[C:21]([CH3:24])[N:20]=[C:19]([NH2:25])[C:18]=2[N:17]=[C:16]1[CH2:26][O:27][CH2:28][CH3:29].C(N(CC)CC)C>C(Cl)(Cl)Cl>[NH2:25][C:19]1[C:18]2[N:17]=[C:16]([CH2:26][O:27][CH2:28][CH3:29])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:8])[C:23]=2[CH:22]=[C:21]([CH3:24])[N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 129729601-(4-aminobutyl)-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10194141N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}morpholine-4-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-Morpholinecarbonyl chloride (202 μL, 1.73 mmol) was added to a solution of 1-(4-aminobutyl)-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-4-amine (0.435, 1.57 mmol) in a mixture of triethylamine (280 μL, 2.04 mmol) and chloroform (8 mL). The reaction mixture was stirred at ambient temperature for 4 hours then it was diluted with chloroform (20 mL) and washed with saturated sodium bicarbonate (10 mL). The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography (30 g of silica gel eluting with 1 L of 2% methanol in chloroform containing 0.5% triethylamine. The resulting glassy solid was triturated with acetonitrile to provide 0.417 g of N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}morpholine-4-carboxamide as an off white powder, m.p. 156.5-159.5° C.

Workup

  1. washwashed with saturated sodium bicarbonate (10 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (30 g of silica gel eluting with 1 L of 2% methanol in chloroform containing 0.5% triethylamine
  5. customThe resulting glassy solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-78034feeb3c54361b6fae993ec03a26c
Source dataset
uspto-grants-2005_06
Patent number
US06903113B2

Linked notes

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