Dazoxiben → HCID 9913269, compound

HRID 1369511Notes

Reaction equation

HRID 1369511 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N:20]1([CH2:25][CH2:26][O:27][C:28]2[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=2)[CH:24]=[CH:23][N:22]=[CH:21]1>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[CH:3][C:2]=1[NH:1][C:32](=[O:33])[C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 53001DazoxibenHCID 16793499HCID 16793499, compound

Product 1

HCID 9913269HCID 9913269, compoundYield 75%

Procedure

Using an analogous procedure to that described in Example 14, N-(3-amino-4-chlorophenyl)-4-cyanobenzamide was reacted with 4-[2-(imidazol-1-yl)ethoxy]benzoic acid (J. Med. Chem., 1985, 28, 1427) to give the title compound in 75% yield; NMR Spectrum: (DMSOd6) 4.48 (t, 2H), 4.65 (m, 2H), 7.09 (d, 1H), 7.51 (d, 1H), 7.68 (m, 3H), 7.82 (s, 1H), 8.0 (m, 4H), 8.1 (m, 2H), 8.73 (d, 1H), 9.18 (s, 1H), 9.89 (s, 1H), 10.66 (s, 1H); Mass Spectrum: M−H− 484.

Sources & evidence

ORD record
ord-902a723b415f432aae3b12676c21846e
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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