Morpholine → HCID 24948587, compound

HRID 1783791Notes

Reaction equation

HRID 1783791 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[N:15]1([CH2:21][CH2:22][C:23]2[N:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]3=[C:25]([C:32](Cl)=[O:33])[N:24]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(Cl)Cl>[N:1]1([C:32]([C:25]2[N:24]=[C:23]([CH2:22][CH2:21][N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[N:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=23)=[O:33])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86617456HCID 86617456, compound

Product 1

HCID 24948587HCID 24948587, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of morpholine (0.050 mL, 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 (85 mg, 55%). 1H NMR (DMSO-d6) δ 8.35 (1H), 8.05 (1H), 7.08 (1H), 6.85 (1H), 3.65 (4H), 4.05 (4H), 3.53 (4H), 3.18 (2H), 2.75 (2H), 2.45 (4H); m/z (M+H)=345.21.

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-62535478035b4277b4d3fd555068c463
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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