Triethylamine → HCID 24948588, compound

HRID 1783792Notes

Reaction equation

HRID 1783792 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[N:18]1([CH2:24][CH2:25][C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[C:28]([C:35](Cl)=[O:36])[N:27]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:35]([C:28]2[N:27]=[C:26]([CH2:25][CH2:24][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=23)=[O:36])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 86617456HCID 86617456, compound

Product 1

HCID 24948588HCID 24948588, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chlorobenzylamine (0.080 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, 47%). 1H NMR (DMSO-d6) δ 8.52 (1H), 8.35 (1H), 8.05 (1H), 7.35 (4H), 7.08 (1H), 6.85 (1H), 4.45 (2H), 3.58 (4H), 3.20 (2H), 2.78 (2H), 2.45 (4H); m/z (M+H)=399.16.

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-e2a611103444467fa6aa8fa54051b481
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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