1-(1,3-Dioxolan-2-yl)methanamine → 2-{[(1,3-Dioxolan-2-ylmethyl)-amino]-methyl}imidazo[1,2-a]pyridine-7-carbonitrile

HRID 908260Notes

Reaction equation

HRID 908260 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].Cl.Cl[CH2:10][C:11]1[N:12]=[C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]2[CH:21]=1>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][CH2:10][C:11]1[N:12]=[C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]2[CH:21]=1

Participants

4

Reactant 2

HCID 108553941-(1,3-Dioxolan-2-yl)methanamineHCID 671323142-(Chloromethyl)imidazo[1,2-a]pyridine-7-carbonitrile hydrochloride2×

Product 1

HCID 671348252-{[(1,3-Dioxolan-2-ylmethyl)-amino]-methyl}imidazo[1,2-a]pyridine-7-carbonitrileYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM solution of 1-(1,3-dioxolan-2-yl)methanamine (799 mg, 7.83 mmol) was added 2-(chloromethyl)imidazo[1,2-a]pyridine-7-carbonitrile hydrochloride (Intermediate 17) (500 mg, 2.61 mmol). After heating to reflux for 1 hr, the reaction mixture was cooled room temperature, concentrated under reduced pressure, chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM) to give the title compound as oil (410 mg). LC/MS: m/z 259(M+H).

Workup

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

Sources & evidence

ORD record
ord-8832b66bb9d54e37aa58dc0a98872bb1
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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