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4-Aminopyridine → HCID 59624858, compound

HRID 1943437
Notes
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Reaction equation

HRID 1943437 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[C:5]2[N:6]([C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=2)[N:7]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[N:53]1[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[C:5]2[N:6]([C:8]([C:11]([NH:59][C:56]3[CH:57]=[CH:58][N:53]=[CH:54][CH:55]=3)=[O:13])=[CH:9][N:10]=2)[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59624777HCID 59624777, compound

Product 1

HCID 59624858HCID 59624858, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A solution of 6-chloro-8-((4-methoxybenzyl)(5-methylpyridin-2-yl)amino)imidazo[1,2-b]pyridazine-3-carboxylic acid (0.07 g, 0.165 mmol), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (0.047 g, 0.248 mmol), 1-hydroxybenzotriazole (0.033 g, 0.248 mmol), TEA (0.069 mL, 0.495 mmol) and pyridin-4-amine (0.023 g, 0.248 mmol) in acetonitrile (2 mL) was heated to 80° C. for 16 hours. The solution was quenched with EA/water. The organic layer was washed with sat NaHCO3 and sat NaCl. The organic layer was dried with Na2SO4, filtered and concentrated in vacuo to give the crude product mixture. The crude product was purified by ISCO (5% EtOAC/DCM; 12 g column), followed by ISCO (5% MeOH/DCM; 12 g column) to afford the title compound (32 mg). [M+H]=500.

Workup

  1. customThe solution was quenched with EA/water
  2. washThe organic layer was washed with sat NaHCO3
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product mixture
  7. customThe crude product was purified by ISCO (5% EtOAC/DCM; 12 g column)

Sources & evidence

ORD record
ord-88ed22ca373048f79c5e14a41beb4674
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08389527B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes