2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoic acid → 2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-N-(1H-tetrazol-5-yl)-benzamide
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]([CH:30]4[CH2:32][CH2:31]4)[CH2:22][CH2:21]3)=[O:19])=[CH:16][N:15]=[C:14]([CH3:33])[CH:13]=2)[C:8]([Cl:34])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:35][C:36]1[NH:40][N:39]=[N:38][N:37]=1>>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]([CH:30]4[CH2:31][CH2:32]4)[CH2:22][CH2:21]3)=[O:19])=[CH:16][N:15]=[C:14]([CH3:33])[CH:13]=2)[C:8]([Cl:34])=[CH:7][C:3]=1[C:4]([NH:35][C:36]1[NH:40][N:39]=[N:38][N:37]=1)=[O:6]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in analogy to Example 39, from 2,5-dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoic acid (Example 66) and 5-amino-1H-tetrazole (commercially available, CAS RN 4418-61-5). The compound was purified twice by preparative HPLC (Phenomenex Gemini column) with a gradient of acetonitrile:water (containing 0.05% formic acid) (50:50 to 95:5) to give 17 mg (15%) of the title compound as a white solid. MS (ESI): m/z=563.109 [M+H]+.
Workup
- customThe compound was purified twice by preparative HPLC (Phenomenex Gemini column) with a gradient of acetonitrile
Sources & evidence
- ORD record
- ord-ded98ce7950f41adae6c6d95a70162ad
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420647B2
Reaction notes
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