Oxalyl chloride → HCID 71280770, compound

HRID 405770Notes

Reaction equation

HRID 405770 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:23]([O:25][CH3:26])=[O:24]>ClCCl.CN(C=O)C.C(N(CC)CC)C>[N:1]1[CH:2]=[C:3]([C:10]([NH:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:23]([O:25][CH3:26])=[O:24])=[O:12])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 337778Methyl 3-amino-4-methylbenzoate

Product 1

HCID 71280770HCID 71280770, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Procedure

To a suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (4.09 g, 25.3 mmol) in dichloromethane (100 mL) and DMF (0.25 mL) at 0° C. was added oxalyl chloride (4.15 mL, 48.0 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and stirred until complete conversion was detected by LCMS. The reaction was subsequently reduced to dryness and suspended in dichloromethane (100 mL) and was added a solution of methyl 3-amino-4-methylbenzoate (2) (4.6 g, 27.9 mmol) in dichloromethane (100 mL) and triethylamine (7.1 mL). Contents were stirred at room temperature for 4 hours and diluted with dichloromethane (100 mL). The reaction was washed with water, saturated NaHCO3, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude solid was triturated with diethyl ether to remove excess aniline and dried to afford methyl 3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate (3) as a white solid. MS m/z 310.1 (M+1)+.

Workup

  1. stirringContents were stirred at room temperature for 4 hours
  2. washThe reaction was washed with water, saturated NaHCO3, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe crude solid was triturated with diethyl ether
  6. customto remove excess aniline
  7. customdried

Sources & evidence

ORD record
ord-fc277cc9114149c997a0b5d83012bac4
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

Loading…