3-Aminopyridine → HCID 67107212, compound

HRID 1623754Notes

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]=[C:22]([Cl:26])[CH:21]=2)=[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]=[C:22]([Cl:26])[CH:21]=2)=[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

Conditions

Temperature: 20 °C

Procedure

Solid pyridin-3-amine (110 mg, 1.17 mmol) was added in one charge to a stirred solution of 5-bromo-2-{[(3-chlorophenyl)methyl]oxy}benzoic acid (may be prepared as described in Description 22; 200 mg, 0.59 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (135 mg, 0.70 mmol) and 1-Hydroxybenzotriazole (95 mg, 0.70 mmol) in DMF (20 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), 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. 70 mg.

Workup

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

Sources & evidence

ORD record: ord-a4aad7d954f64bf1ad46677aecc15378
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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