Triethylamine → HCID 24948781, compound

HRID 1783796Notes

Reaction equation

HRID 1783796 reaction equation
NC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH2:9]([N:11](CC)CC)C.Cl.[N:17]1([CH2:23][CH2:24][C:25]2[N:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]3=[C:27]([C:34](Cl)=[O:35])[N:26]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(Cl)Cl>[N:4]1[CH:3]=[CH:8][CH:7]=[C:6]([CH2:9][NH:11][C:34]([C:27]2[N:26]=[C:25]([CH2:24][CH2:23][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=23)=[O:35])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 86617456HCID 86617456, compound

Product 1

HCID 24948781HCID 24948781, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(aminomethyl)pyridine (0.052 g, 0.54 mmol) and triethylamine (0.16 mL, 1.14 mmol) in CH2Cl2 (10 mL) was added 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carbonyl chloride hydrochloride (150 mg, 0.45 mmol). The mixture was stirred at ambient temperature for 1 h then washed with sat. aq. NaHCO3 (20 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (20 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (52 mg, 32%). 1H NMR (DMSO-d6) δ 8.50 (2H), 8.35 (1H), 8.05 (1H), 7.54 (1H), 7.32 (1H), 7.25 (1H), 78.08 (1H), 6.85 (1H), 4.59 (2H), 3.57 (4H), 3.20 (2H), 2.80 (2H), 2.43 (4H); m/z (M+H)=366.15.

Workup

  1. washthen washed with sat. aq. NaHCO3 (20 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (20 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-0bb66c627985473abead64a2bfa9e38c
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

Loading…