3-Aminopyridine → HCID 580694, compound

HRID 1623757Notes

Reaction equation

HRID 1623757 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[C:13]([CH:17]=1)[C:14](O)=[O:15].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[C:13]([CH:17]=1)[C:14]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:15]

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 87070765-bromo-2-[(2-chlorobenzyl)oxy]benzoic acid

Product 1

HCID 580694HCID 580694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Solid pyridin-3-amine (212 mg, 2.25 mmol) was added in one charge to a stirred solution of 5-bromo-2-{[(2-chlorophenyl)methyl]oxy}benzoic acid (may be prepared as described in Description 28; 350 mg, 1.03 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (236 mg, 1.23 mmol) and 1-Hydroxybenzotriazole (166 mg, 1.23 mmol) in DMF (20 ml) under nitrogen at 20° C. The reaction mixture was stirred at 20° C. for 16 h. Water (50 ml) was added to the mixture and the mixture was filtered to yield the title compound as a white solid. 400 mg.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-576076282a5a4de08ad6d861e8e7383c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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