Triethylamine → HCID 22923866, compound

HRID 2258311Notes

Reaction equation

HRID 2258311 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:11]=[C:12]([O:20][CH3:21])[C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1)([OH:9])=O.C(N(CC)CC)C.[CH2:29]([O:33][CH2:34][CH2:35][CH2:36][NH2:37])[CH2:30][CH2:31][CH3:32]>CN(C)C=O.O1CCCC1.ClCCl>[CH2:29]([O:33][CH2:34][CH2:35][CH2:36][NH:37][C:7]([C:10]1[CH:11]=[C:12]([O:20][CH3:21])[C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=1)=[O:9])[CH2:30][CH2:31][CH3:32]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 854611-Propanamine, 3-butoxy-HCID 22923859Methyl 5-carboxy-3-methoxypyridine-2-carboxylate

Product 1

HCID 22923866HCID 22923866, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1.7 ml of oxalyl chloride (20 mmol), and also 2 drops of N,N-dimethylformamide, dissolved in tetrahydrofuran, were added dropwise, at 10° C. and while stirring, to 2.1 g (10 mmol) of methyl 5-carboxy-3-methoxypyridine-2-carboxylate in 100 ml of anhydrous tetrahydrofuran and the reaction mixture was stirred at 10° C. for 30 min and at 20° C. for 1 h. It was then concentrated and the residue was dissolved in dichloromethane; 6.8 ml (50 mmol) of triethylamine, and then 1.3 g (1.5 ml, 10 mmol) of 3-butoxypropylamine, dissolved in dichloromethane, were added, at 0° C., to this solution.

Workup

  1. additionwere added dropwise, at 10° C.
  2. concentrationIt was then concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionwere added, at 0° C., to this solution

Sources & evidence

ORD record
ord-fc540e5e366840bcae3c153810d636f2
Source dataset
uspto-grants-1997_08
Patent number
US05658933

Reaction notes

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