Triethylamine → 3-{3-[2-(Dimethylamino)acetylamino]phenyl}-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide
Reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][C:5](O)=[O:6].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:28][C:29]1[CH:30]=[C:31]([C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([C:44]([NH2:46])=[O:45])[CH:42]=3)[N:37]([CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)[N:36]=2)[CH:32]=[CH:33][CH:34]=1>ClCCl.CN(C)C=O>[CH3:2][N:3]([CH3:8])[CH2:4][C:5]([NH:28][C:29]1[CH:30]=[C:31]([C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([C:44]([NH2:46])=[O:45])[CH:42]=3)[N:37]([CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)[N:36]=2)[CH:32]=[CH:33][CH:34]=1)=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-(dimethylamino)acetic acid hydrochloride (0.091 g, 0.649 mmol) in 6 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.135 g, 0.708 mmol) and triethyl amine (0.090 mL, 0.649 mmol). The reaction was stirred at room temperature for 10 min before 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (0.200 g, 0.59 mmol) dissolved in 1 mL of dichloromethane, was added to the solution. Dimethyl formamide (2 mL) was added to aid solubility. Additional reagent (1 equivalent) was necessary to drive the reaction to completion. The reaction mixture was then partitioned between water and dichloromethane. The crude material that was obtained from evaporation of the extracts was not purified further. (Yield not calculated) ES-MS (m/z) 422 [M+H]+.
Workup
- additionwas added to the solution
- customthe reaction to completion
- customThe reaction mixture was then partitioned between water and dichloromethane
Sources & evidence
- ORD record
- ord-aca60054149b4dfba7e478a3d6720870
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06897231B2
Reaction notes
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