Triethylamine → 3-((4-(4-Amino-5-chloro-2-ethoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide
Reaction equation
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[NH2:19][C:20]1[C:28]([Cl:29])=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22]([O:30][CH2:31][CH3:32])[CH:21]=1.[C:33]([NH:37][C:38](=[O:52])[C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:40]=1)([CH3:36])([CH3:35])[CH3:34].C(N(CC)CC)C>ClCCl>[NH2:19][C:20]1[C:28]([Cl:29])=[CH:27][C:23]([C:24]([N:49]2[CH2:48][CH2:47][N:46]([CH2:45][C:41]3[CH:40]=[C:39]([CH:44]=[CH:43][CH:42]=3)[C:38]([NH:37][C:33]([CH3:35])([CH3:36])[CH3:34])=[O:52])[CH2:51][CH2:50]2)=[O:26])=[C:22]([O:30][CH2:31][CH3:32])[CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Propanephosphonic acid cyclic anhydride (5.90 g, 9.2 mmol, 5.52 mL) was added dropwise to a solution of 4-ammo-5-chloro-2-ethoxy benzoic acid (1 g, 4.6 mmol), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1.40 g, 5.1 mmol) and triethylamine (1.401 g, 13.8 mmol, 1.93 mL) in dichloromethane. The reaction mixture was stirred at room temperature for 2 hours. The reaction was concentrated under reduced pressure and the residue was taken up in ethyl acetate, washed with water, sodium hydrogen carbonate and brine. The organic phase was concentrated under vacuum to afford the title compound (2.08 g).
Workup
- concentrationThe reaction was concentrated under reduced pressure
- washwashed with water, sodium hydrogen carbonate and brine
- concentrationThe organic phase was concentrated under vacuum
Sources & evidence
- ORD record
- ord-83da8fae4dfe46ea8d698f3dd0738f2f
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314091B2
Reaction notes
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