N1-(pyridin-2-yl)benzene-1,2-diamine → HCID 22736762, compound

HRID 50910Notes

Reaction equation

HRID 50910 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].[S:15]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22](Cl)=O)=[CH:16]1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=[C:22]1/[CH:21]=[CH:20]/[C:17]1[CH:18]=[CH:19][S:15][CH:16]=1

Participants

4

Reactant 3

HCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 123365123-(3-Thienyl)-acryloyl chloride

Product 1

HCID 22736762HCID 22736762, compound

Procedure

The titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-(3-thienyl)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: 303.39; mp: 135.5-136.0° C.; 1H-NMR (CDCl3) δ: 8.77 (1H, ddd, J=5.1, 1.8, 0.7 Hz), 8.03-7.95 (2H, m), 7.84-7.80 (1H, m), 7.54-7.43 (4H, m), 7.38-7.24 (4H, m), 6.97 (1H, d, J=15.7 Hz).

Sources & evidence

ORD record
ord-026cbfe1adb84eafbf5b6e280284d8a1
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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