3-Aminopyridine → HCID 67108054, compound

HRID 1623764Notes

Reaction equation

HRID 1623764 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[C:26]#[N:27])=[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>[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[C:26]#[N:27])=[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

6

Reactant 4

HCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28830820HCID 28830820, compound

Product 1

HCID 67108054HCID 67108054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Solid pyridin-3-amine (91 mg, 0.96 mmol) was added in one charge to a stirred solution of 5-bromo-2-{[(2-cyanophenyl)methyl]oxy}benzoic acid (may be prepared as described in Description 34; 160 mg, 0.48 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (111 mg, 0.58 mmol) and 1-Hydroxybenzotriazole (78 mg, 0.58 mmol) in DMF (15 ml) under nitrogen at 20° C. The reaction mixture was stirred at 20° C. for 16 h. The organic phase was washed with water (25 ml), and extracted with ethyl acetate (3×30 ml), dried over sodium sulphate, evaporated in vacuo and purified by column chromatography (petroleum ether:ethyl acetate=2:1) to yield the title compound as a white solid. 180 mg.

Workup

  1. washThe organic phase was washed with water (25 ml)
  2. extractionextracted with ethyl acetate (3×30 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo
  5. custompurified by column chromatography (petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-40897914a08f4e718cd9c0b99f286854
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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