Diisopropylethylamine → N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide
Reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.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.[Br:43][C:44]1[CH:45]=[C:46]([NH2:53])[C:47]2[CH:48]=[N:49][NH:50][C:51]=2[CH:52]=1>CN(C=O)C>[Br:43][C:44]1[CH:52]=[C:51]2[C:47]([CH:48]=[N:49][NH:50]2)=[C:46]([NH:53][C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)=[O:9])[CH:45]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
2-Methyl-1,3-thiazole-4-carboxylic acid (4.59 g, 32.1 mmol), HATU (13.4 g, 35.3 mmol) and DIPEA (16.8 ml, 96 mmol) were stirred in DMF (140 ml) for 30 mins at 20° C. 6-Bromo-1H-indazol-4-amine (3.40 g, 16.03 mmol) was added and the reaction stirred at 20° C. for 2 days. The solvent was reduced to ˜40 ml and the reaction mixture applied to 5×70 g aminopropyl SPE cartridges and left to stand for 3 h. The cartridges were eluted with DCM:MeOH (1:1, v/v) and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-15% MeOH (containing 1% Et3N) in DCM. Appropriate fractions were evaporated to give the title compound 1.02 g.
Workup
- waitleft
- waitto stand for 3 h
- washThe cartridges were eluted with DCM:MeOH (1:1
- customv/v) and the solvent was evaporated in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with 0-15% MeOH (containing 1% Et3N) in DCM
- customAppropriate fractions were evaporated
Sources & evidence
- ORD record
- ord-c6befc9b258d47f0bfa8f9d198714a69
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163743B2
Reaction notes
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