N-Methylaniline → HCID 24948589, compound

HRID 1783793Notes

Reaction equation

HRID 1783793 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(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>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:34]([C:27]1[N:26]=[C:25]([CH2:24][CH2:23][N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[N:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=12)=[O:35]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 86617456HCID 86617456, compound

Product 1

HCID 24948589HCID 24948589, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of n-methylaniline (0.060 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 (105 mg, 64%). 1H NMR (DMSO-d6) δ 8.23 (1H), 8.00 (1H), 7.30 (2H), 7.19 (3H), 7.05 (1H), 6.81 (1H), 3.52 (4H), 3.48 (3H), 2.95 (2H), 2.45 (2H), 2.33 (4H); m/z (M+H)=365.26.

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-15ed0b16e08a4af98179572a7066b8aa
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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