2-(Imidazo(1,2-a)pyridin-2-yl)ethan-1-amine → 7-Chloro-2-(2-imidazo[1,2-a]pyridin-2-yl-ethyl)-5-methyl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dione

HRID 1752601Notes

Reaction equation

HRID 1752601 reaction equation
[N:1]1[C:2]([CH2:10][CH2:11][NH2:12])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:13][N:14]1[CH:19]=[C:18]([CH2:20]Cl)[C:17]([C:22](OC)=[O:23])=[C:16]([Cl:26])[C:15]1=[O:27]>CC#N>[Cl:26][C:16]1[C:15](=[O:27])[N:14]([CH3:13])[CH:19]=[C:18]2[CH2:20][N:12]([CH2:11][CH2:10][C:2]3[N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]4[CH:3]=3)[C:22](=[O:23])[C:17]=12

Participants

4

Reactant 2

HCID 75365162-(Imidazo(1,2-a)pyridin-2-yl)ethan-1-amineHCID 904216921-Methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine2×

Product 1

HCID 904219587-Chloro-2-(2-imidazo[1,2-a]pyridin-2-yl-ethyl)-5-methyl-3,5-dihydro-2H-pyrrolo[3,4-c]pyridine-1,6-dioneYield 48.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

TEA (5 ml, 36 mmol) was added to a suspension of 2-(imidazo[1,2-a]pyridine-2-yl)ethanamine (1.934 g, 12 mmol) and 1-methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine (3 g, 12 mmol, see compound (6) of Example b1)) in MeCN (5 ml). The reaction was heated in a CEM microwave at about 100° C. for about 40 min. The solvent was removed and the resulting mixture was deposited onto silica gel, loaded onto a silica gel column and eluted with DCM/MeOH (50:1) to give 2.9 g of crude product. The crude product was washed with water, dried to afford the title compound (2 g, 5.76 mmol, 48.1% yield).

Workup

  1. customThe solvent was removed
  2. washeluted with DCM/MeOH (50:1)
  3. customto give 2.9 g of crude product
  4. washThe crude product was washed with water
  5. customdried

Sources & evidence

ORD record
ord-2b8c016345c8414a95029a0c1b92dc61
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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