Carbonate Ion → 2-Chloro-5-(5-cyclopropyl-1H-pyrazol-3-yl)-N-(1-hydroxy-cycloheptylmethyl)-benzamide
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:19][CH2:20][C:21]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C1C=CC=CN=1)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)=[CH:7][C:3]=1[C:4]([NH:19][CH2:20][C:21]1([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:6]Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-chloro-5-(5-cyclopropyl-1H-pyrazol-3-yl)-benzoic acid (0.06 g, 0.23 mmol), 1-aminomethyl-cycloheptanol ((0.082 g, 0.46 mmol), polystyrene supported carbonyldiimidazole (0.37 g, 0.46 mmol), polystyrene supported dimethylaminopyridine (0.32 g, 0.46 mmol) and 1-hydroxybenztriazole (0.06 g, 0.46 mmol) in N,N-dimethylformamide (3 mL) was shaken at room temperature for 16 h. MP-carbonate was added (0.5 g) and the resulting mixture was shaken at room temperature for 2 h. The mixture was filtered and the filtrate was concentrated in vacuo. the residue was purified by reverse phase chromatography to afford the title compound (0.02 g). LCMS (m/z) 388.4 M+1.
Workup
- stirringthe resulting mixture was shaken at room temperature for 2 h
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- customthe residue was purified by reverse phase chromatography
Sources & evidence
- ORD record
- ord-b6635384c16a436289ed11e206891357
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186742B2
Reaction notes
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