Oxalyl chloride → N3-(5-Chlorothiophen-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine

HRID 397544Notes

Reaction equation

HRID 397544 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30]3[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:36][C:35]2[C:30]([NH:29][CH2:28][CH:25]3[CH2:26][CH2:27][N:22]([C:19]4[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=4)[CH2:23][CH2:24]3)=[N:31][CH:32]=[CH:33][CH:34]=2)=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 65578Oxalyl chlorideHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 12150690N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine

Product 1

HCID 12990572N3-(5-Chlorothiophen-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamineYield 62.3%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chlorothiophene-2-carboxylic acid (120 mg, 0.72 mmol) in methylene chloride and DMF (0.005 mL) was treated with oxalyl chloride (0.105 mL, 1.20 mmol). After 0.25 h, the mixture was concentrated and the residue was dissolved in chloroform. This solution was added dropwise to a solution of N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine (170 mg, 0.6 mmol) in pyridine and chloroform. The reaction mixture was then purified using a procedure similar to that described in Example 2, Part D, yielding 160 mg (58%) of the title compound as a hydrochloride salt.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. customThe reaction mixture was then purified

Sources & evidence

ORD record
ord-116baf5411ef42248885d81115a452db
Source dataset
uspto-grants-2003_08
Patent number
US06610704B1

Reaction notes

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