Aniline → HCID 24771608, compound

HRID 1952199Notes

Reaction equation

HRID 1952199 reaction equation
Cl.CN(C)CCCN=C=NCC.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.[CH3:23][C:24]1[C:25]2[N:26]([CH:30]=[C:31]([C:33](O)=[O:34])[N:32]=2)[CH:27]=[CH:28][CH:29]=1.NC1C=CC=CC=1>ClCCl.O.C(N(CC)CC)C>[CH3:23][C:24]1[C:25]2[N:26]([CH:30]=[C:31]([C:33]([NH:14][C:18]3[CH:17]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:34])[N:32]=2)[CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27598608-methylimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 24771608HCID 24771608, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.67 ml of triethylamine, 1.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.08 g of 1-hydroxybenzotriazole are added to a solution of 0.176 g of 8-methylimidazo[1,2-a]pyridine-2-carboxylic acid in 12 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 20 minutes. 0.090 ml of aniline is added. The reaction mixture is stirred at ambient temperature for 4 hours. 60 ml of dichloromethane and 30 ml of water are added. After separation by settling, the organic phase is dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. After purifying by flash chromatography (silica, eluent dichloromethane/ethyl acetate 98/02 by volume), 0.193 g of 8-methyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide is obtained in the form of a white solid.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 4 hours
  2. customAfter separation
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customAfter purifying by flash chromatography (silica, eluent dichloromethane/ethyl acetate 98/02 by volume)

Sources & evidence

ORD record
ord-dabbcb4af0bb4b46850cd61445a14e3f
Source dataset
uspto-grants-2013_03
Patent number
US08404848B2

Reaction notes

Loading…