Dimethylformamide → HCID 58374814, compound

HRID 1043686Notes

Reaction equation

HRID 1043686 reaction equation
CN(C=O)C.[CH:6]1([C:9]([NH:11][C:12]2[N:29]=[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([C:20]4[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=4)[N:14]3[N:13]=2)=[O:10])[CH2:8][CH2:7]1.C(Cl)(=O)C([Cl:33])=O>C(Cl)Cl>[CH:6]1([C:9]([NH:11][C:12]2[N:29]=[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([C:20]4[CH:28]=[CH:27][C:23]([C:24]([Cl:33])=[O:25])=[CH:22][CH:21]=4)[N:14]3[N:13]=2)=[O:10])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 42597466HCID 42597466, compound

Product 1

HCID 58374814HCID 58374814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 Drops of DMF are added to a solution of 4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzoic acid (1 eq) obtained by Method A using 4-carboxyphenylboronic acid in DCM under N2 atmosphere. Then oxalyl chloride (2 eq) is added dropwise to this resulting solution (gas release). The mixture is stirred at room temperature for 2 hours. After completion of the reaction by LCMS, the solvent is removed. The crude acid chloride is used without further purification in next step.

Workup

  1. customAfter completion of the reaction by LCMS
  2. customthe solvent is removed
  3. customThe crude acid chloride is used without further purification in next step

Sources & evidence

ORD record
ord-3d8439c4744e4f1d8f83c0c7528d7d53
Source dataset
uspto-grants-2013_10
Patent number
US08563545B2

Reaction notes

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