Triethylamine → HCID 59376069, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:5](=[O:14])[CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[C:11]([OH:13])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[CH2:43]([N:45]([CH2:49][CH3:50])[CH2:46][CH2:47][NH2:48])[CH3:44]>CN(C=O)C>[CH2:43]([N:45]([CH2:49][CH3:50])[CH2:46][CH2:47][NH:48][C:11]([C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:14])[C:4]=2[NH:3][C:2]=1[CH3:1])=[O:13])[CH3:44]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) 0.2 g (1.0 mmol), HOBt 0.16 g (1.2 mmol), EDCI 0.24 g (1.2 mmol) and triethylamine 0.2 g (2.0 mmol) in 10 ml DMF was stirred at room temperature for 20 min, then N1,N1-diethylethane-1,2-diamine 0.24 g (2.1 mmol) was added. After stirred at room temperature for 24 hours, the mixture was poured into the ice water and extracted with CH2Cl2. The organic layer separated was washed with water and saturated sodium chloride solution, then dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column, eluted with CH2Cl2/MeOH (30:1), to give 0.23 g (79%) of the titled compound as a white solid.
Workup
- stirringAfter stirred at room temperature for 24 hours
- extractionextracted with CH2Cl2
- customThe organic layer separated
- washwas washed with water and saturated sodium chloride solution
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column
- washeluted with CH2Cl2/MeOH (30:1)
Sources & evidence
- ORD record
- ord-44e20dc18ead4e1e8b049030568098f1
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084621B2
Reaction notes
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