Propylamine → HCID 18457829, compound

HRID 747566Notes

Reaction equation

HRID 747566 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]([C:18]([OH:20])=O)[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].C(Cl)(=O)C(Cl)=O.[CH2:27]([NH2:30])[CH2:28][CH3:29]>C(Cl)(Cl)Cl>[CH3:17][C:16]1[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)=[CH:12][C:13]([C:18]([NH:30][CH2:27][CH2:28][CH3:29])=[O:20])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 65578Oxalyl chlorideHCID 18457813HCID 18457813, compound

Product 1

HCID 18457829HCID 18457829, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4′-(Methoxycarbonyl)-6-methyl-1,1′-biphenyl-3-carboxylic acid (190 mg, 0.7 mmol) and oxalyl chloride (70 μl, 0.77 mol) in chloroform (4 ml) were stirred at room temperature for 15 min. Propylamine (200 μl) was added and stirring continued for 45 min. The reaction was quenched with water (4 ml), the phases separated and the organic phase passed through an aminopropyl SPE eluting with chloroform. After evaporation of the solvent this gave methyl 6′-methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylate (216 mg). LCMS: retention time 3.26 min, MH+312.

Workup

  1. customThe reaction was quenched with water (4 ml)
  2. customthe phases separated
  3. washeluting with chloroform
  4. customAfter evaporation of the solvent this gave methyl 6′-methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylate (216 mg)

Sources & evidence

ORD record
ord-301b27e69f68456188d414a8292b2ba4
Source dataset
uspto-grants-2008_07
Patent number
US07396843B2

Reaction notes

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