3-Aminopyridine → HCID 68108924, compound

HRID 1623755Notes

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][C:23]([C:26]#[N:27])=[CH:22][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:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=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 (82 mg, 0.873 mmol) was added in one charge to a stirred solution of 5-bromo-2-{[(4-cyanophenyl)methyl]oxy}benzoic acid (may be prepared as described in Description 24; 145 mg, 0.44 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (100 mg, 0.52 mmol) and 1-Hydroxybenzotriazole (70.8 mg, 0.52 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), 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. 100 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-29a1f66b6383420e829a5350a707d93b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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