Diisopropylethylamine → 5-[2-({[(6-chloropyridin-3-yl)methyl]amino}methyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one

HRID 552912Notes

Reaction equation

HRID 552912 reaction equation
Cl[CH2:2][C:3](=[CH2:16])[CH2:4][CH:5]1[O:9][C:8](=[O:10])[CH:7]=[C:6]1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[Cl:17][C:18]1[N:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[Cl:17][C:18]1[N:23]=[CH:22][C:21]([CH2:24][NH:25][CH2:2][C:3](=[CH2:16])[CH2:4][CH:5]2[O:9][C:8](=[O:10])[CH:7]=[C:6]2[N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 671658135-[2-(chloromethyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one

Product 1

HCID 866324425-[2-({[(6-chloropyridin-3-yl)methyl]amino}methyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-oneYield 75.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At 60° C., 600 mg (2.48 mmol) of 5-[2-(chloromethyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one (V-1a), 354 mg (2.48 mmol) of 1-(6-chloropyridin-3-yl)methanamine and 0.43 ml (2.48 mmol) of N-ethyl-N-isopropylpropan-2-amine in 10 ml of acetonitrile are stirred for 21 hours. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture dichloromethane:methanol (98:2 to 90:10) gives 650 mg (73% of theory) of 5-[2-({[(6-chloropyridin-3-yl)methyl]amino}methyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one.

Workup

  1. concentrationConcentration
  2. customunder reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-2f15c30d269c4425af5f80fa9de92c60
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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