Methylamine → 5-[5-(N-methylcarbamoyl)pentyl]imidazo[1,5-a]pyridine

HRID 326120Notes

Reaction equation

HRID 326120 reaction equation
C(O[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:5])C.[CH3:20][NH2:21]>C(O)CCC>[CH3:20][NH:21][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 132061385-(5-Ethoxycarbonylpentyl)imidazo[1,5-a]pyridine

Product 1

HCID 132061445-[5-(N-methylcarbamoyl)pentyl]imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 3.9 g of 5-(5-ethoxycarbonylpentyl)-imidazo[1,5-a]pyridine in 40 ml of n-butanol is saturated with methylamine and heated on a steam bath for 56 hours in a pressure bottle. The reaction mixture is evaporated to dryness; the resulting product is first crystallized from ether and then recrystallized from 1:1 ethyl acetate-ether to yield the 5-[5-(N-methylcarbamoyl)pentyl]-imidazo[1,5-a]pyridine melting at 118°-22°.

Workup

  1. temperatureheated on a steam bath for 56 hours in a pressure bottle
  2. customThe reaction mixture is evaporated to dryness
  3. customthe resulting product is first crystallized from ether
  4. customrecrystallized from 1:1 ethyl acetate-ether

Sources & evidence

ORD record
ord-925320fd79ae4a80a92b4e3b57e3f5e0
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Reaction notes

Loading…