HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 49843
Notes
Print preview

Reaction equation

HRID 49843 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1049
Pyridine
Solvent
HCID 6212ChloroformSolvent
HCID 6228DimethylformamideSolvent
HCID 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-0208a0524ee5473484eeef0ced84e59f
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06710057B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes