Diisopropylethylamine → 4-(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-methyl-1H-indole-6-carbonyl)piperazin-2-one
Reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:18]=[N:19][C:20]([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]([OH:34])=O)[CH:30]=3)[C:25]([CH3:35])=[CH:24]2)=[N:21][CH:22]=1.[OH:36][C:37]1SC2C=CC=[CH:42][C:40]=2[N:41]=1.C(=O)([O-])O.[Na+]>ClCCl>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:18]=[N:19][C:20]([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]([N:4]4[CH2:42][CH2:40][NH:41][C:37](=[O:36])[CH2:1]4)=[O:34])[CH:30]=3)[C:25]([CH3:35])=[CH:24]2)=[N:21][CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
EDCxHCl (150 μmol) and N,N-diisopropylethylamine (380 μmol) were added to a solution of 1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-methyl-1H-indole-6-carboxylic acid (100 μmol) and hydroxybenzothiazol (30 μmol) in dichloromethane (4 mL) and the mixture was stirred for 15 min at room temperature. The appropriate amine (125 μmol) was added and the reaction mixture was stirred for 16 h at room temperature. The reaction was stopped by addition of saturated sodium hydrogen carbonate solution (2.5 mL) and the mixture was extracted with dichloromethane (3×3 mL). The solvent was removed under reduced pressure and the residue purified by preparative HPLC to furnish the desired compound.
Workup
- stirringthe reaction mixture was stirred for 16 h at room temperature
- extractionthe mixture was extracted with dichloromethane (3×3 mL)
- customThe solvent was removed under reduced pressure
- customthe residue purified by preparative HPLC
Sources & evidence
- ORD record
- ord-fb80a17e48fc49179acbf3dfebfff757
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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