Triethylamine → HCID 10236927, compound

HRID 1265071Notes

Reaction equation

HRID 1265071 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:19]([CH3:21])=[C:18]([CH3:22])[N:17]=[C:16]([NH2:23])[C:15]=2[N:14]=[C:13]1[CH3:24].[N:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl>[NH2:23][C:16]1[C:15]2[N:14]=[C:13]([CH3:24])[N:12]([CH2:11][CH2:10][CH2:9][NH:8][C:31]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:32])[C:20]=2[C:19]([CH3:21])=[C:18]([CH3:22])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 219460311-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10236927HCID 10236927, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.78 mL, 5.6 mmol) was added to a solution of 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.00 g, 4.3 mmol) in chloroform (50 mL). The solution was cooled in an ice bath and then 4-morpholinecarbonyl chloride (0.55 mL, 4.7 mmol) was added. After 15 minutes the reaction mixture was removed from the ice bath and allowed to stir at ambient temperature for 2 days. The reaction mixture was diluted with water (30 mL) and the pH was adjusted to 11 with potassium carbonate. The resulting precipitate was isolated by filtration and then recrystallized from isopropanol/water to provide 0.61 g of N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]morpholine-4-carboxamide as a white solid, m.p. 128.9-129.7° C. Analysis: Calculated for C17H26N6O2.1.00 H2O: %C, 56.03; %H, 7.74; %N, 23.06; Found: %C, 56.10; %H, 7.92; %N, 23.31. 1H NMR (Bruker 300 MHz, DMSO-d6) δ6.63 (t, J=4.9 Hz, 1H), 5.56 (s, 2 H), 4.19 (t, J=8.1 Hz, 2 H), 3.53 (t, J=4.4 Hz, 4 H), 3.25 (t, J=4.9 Hz, 4 H), 3.14 (q, J=6.2 Hz, 2 H), 2.45 (s, 3 H), 2.35 (s, 3 H), 2.29 (s, 3 H), 1.81 (p, J=7.4 Hz, 2 H). MS(CI) m/e 347 (M+H).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customAfter 15 minutes the reaction mixture was removed from the ice bath
  3. additionThe reaction mixture was diluted with water (30 mL)
  4. customThe resulting precipitate was isolated by filtration
  5. customrecrystallized from isopropanol/water

Sources & evidence

ORD record
ord-08c1385655ad4068b55fff03b612c812
Source dataset
uspto-grants-2003_04
Patent number
US06545017B1

Reaction notes

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