1H-Indazole-3-carboxylic acid, 1-methyl- → 1-Methyl-1H-indazole-3-carboxylic acid{2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[N:3]1.Cl.[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[O:27][C:26]([CH2:28][CH2:29][NH2:30])=[CH:25][CH:24]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]>>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[O:27][C:26]([CH2:28][CH2:29][NH:30][C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[N:3]=3)=[O:13])=[CH:25][CH:24]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]Participants
3
Procedure
The title compound was prepared as in Example 12 starting from N-methyl-indazole-3-carboxylic acid and 2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylamine hydrochloride. The crude product was purified by flash chromatography using heptane/EtOAc as a gradient eluent (9:1-8:2). 1H NMR (400 MHz, DMSO-d6): 3.00 (2H, t), 3.64 (2H, m), 4.12 (3H, s), 6.36 (1H, d), 7.01 (1H, d), 7.26 (1H, m), 7.46 (1H, m), 7.600 (1H, s), 7.602 (1H, s), 7.72 (1H, d), 7.83 (1H, s), 8.16 (1H, d), 8.48 (1H, t).
Workup
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-d28926f872674613a54aeb5b5f93d266
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
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