Water → N-((3-chloropyrazin-2-yl)methyl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxamide
Reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([OH:13])=O)[C:5]=2[CH:4]=[N:3]1.Cl.[Cl:15][C:16]1[C:17]([CH2:22][NH2:23])=[N:18][CH:19]=[CH:20][N:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[Cl:15][C:16]1[C:17]([CH2:22][NH:23][C:11]([CH:6]2[CH2:7][CH2:8][CH2:9][C:10]3[N:2]([CH3:1])[N:3]=[CH:4][C:5]2=3)=[O:13])=[N:18][CH:19]=[CH:20][N:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylic acid (6 g, 33 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (6 g, 33 mmol) in 200 mL of DCM was added TEA (9 g, 88 mmol) dropwise. The resulting mixture was stirred at room temperature for 5 mins, and then HATU (12.5 g, 33 mmol) was added to the solution in portions at 0° C. The mixture was stirred at room temperature for 2 hours. Water was added, the DCM layers was separated, and washed with brine, dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography on silica gel (PE/THF=5/1 v/v %) to afford N-((3-chloropyrazin-2-yl)methyl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxamide (1.5 g, 15%).
Workup
- stirringThe mixture was stirred at room temperature for 2 hours
- customthe DCM layers was separated
- washwashed with brine
- dry with materialdried over Na2SO4
- customThe solvent was removed
- customthe residue was purified by column chromatography on silica gel (PE/THF=5/1 v/v %)
Sources & evidence
- ORD record
- ord-de32ef3e0b3846c680135c0217602ee3
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446130B2
Reaction notes
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