Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-1-methyl-1H-1,2,4-triazole-3-carboxamide
Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:34][N:35]1[CH:39]=[N:38][C:37]([C:40]([OH:42])=O)=[N:36]1.[NH:43]1[C:51]2[C:46](=[C:47]([C:52]3[CH:53]=[C:54]([NH2:61])[C:55]4[CH:56]=[N:57][NH:58][C:59]=4[CH:60]=3)[CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44]1>CN(C=O)C>[NH:43]1[C:51]2[C:46](=[C:47]([C:52]3[CH:60]=[C:59]4[C:55]([CH:56]=[N:57][NH:58]4)=[C:54]([NH:61][C:40]([C:37]4[N:38]=[CH:39][N:35]([CH3:34])[N:36]=4)=[O:42])[CH:53]=3)[CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
HATU (248 mg) and DIPEA (0.211 ml) were added to a flask containing 1-methyl-1H-1,2,4-triazole-3-carboxylic acid (51 mg) in DMF (1 ml). The reaction was stirred for 30 min under nitrogen. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (50 mg) was added and the mixture was stirred for 3 h at RT under nitrogen. The reaction mixture was applied to an aminopropyl SPE cartridge (5 g) and left for 3 h. The column was washed with 10% methanol in DCM. The appropriate fractions were combined and the solvent was evaporated. The residue was dissolved in methanol:DMSO (1 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (37 mg).
Workup
- stirringthe mixture was stirred for 3 h at RT under nitrogen
- waitleft for 3 h
- washThe column was washed with 10% methanol in DCM
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in methanol
- customDMSO (1 ml, 1:1) and purified by mass
Sources & evidence
- ORD record
- ord-569873561e0d48fd9d6fe49fca6c888c
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658635B2
Reaction notes
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