1-(1,3-Dioxolan-2-yl)methanamine → 1-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamine

HRID 908257Notes

Reaction equation

HRID 908257 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].Cl[CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]2[CH:22]=1>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:14][N:13]2[CH:22]=1

Participants

4

Reactant 2

HCID 108553941-(1,3-Dioxolan-2-yl)methanamineHCID 580247822-(Chloromethyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine2×

Product 1

HCID 580248001-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamineYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM 5 mL solution of 1-(1,3-dioxolan-2-yl)methanamine (814 mg, 7.89 mmol) was added 2-(chloromethyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Intermediate 19) (620 mg, 2.63 mmol). After heating to reflux for 1.5 hr, the reaction mixture (suspension) was cooled to room temperature and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM) to give the title compound as solid (450 mg). LC/MS: m/z 302(M+H).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1.5 hr
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM)

Sources & evidence

ORD record
ord-69677bd2a30a43b4a8adc16511e27c99
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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