N1-(pyridin-2-yl)benzene-1,2-diamine → HCID 22736753, compound

HRID 50906Notes

Reaction equation

HRID 50906 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1/[CH:20]=[CH:21]/[C:22](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1/[CH:20]=[CH:21]/[C:22]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Participants

4

Reactant 3

HCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 10920765(2E)-3-(furan-2-yl)prop-2-enoyl chloride

Product 1

HCID 22736753HCID 22736753, compound

Procedure

The titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-(2-furyl)acryloyl chloride (New, J. S.; Christopher, W. L.; Yevich, J. P.; Butler, R.; Schlemmer, R. F.; VanderMaelen, C. P.; Cipollina, J. A. J. Med. Chem., 1989, 32, 1147) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 287.32; mp: 164.0-165.0° C.; 1H-NMR (CDCl3) δ: 8.80-8.75 (1H, m), 8.00 (1H, ddd, J=7.7, 7.7, 1.8 Hz), 7.83-7.78 (1H, m), 7.78 (1H, d, J=15.4 Hz), 7.54-7.39 (4H, m), 7.37-7.16 (2H, m), 7.01 (1H, d, J=15.4 Hz), 6.51 (1H, d, J=3.3 Hz), 6.44 (1H, dd, J=3.3, 1.8 Hz).

Sources & evidence

ORD record
ord-ca879f38964b4a91a58774b8d9e54a72
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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