1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(2H-[1,2,3]triazol-4-yl)-benzamide
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[N:14][NH:13][N:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.[NH2:38][CH2:39][C:40]1([OH:47])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1.C(=O)([O-])[O-]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[N:14][NH:13][N:12]=2)=[CH:7][C:3]=1[C:4]([NH:38][CH2:39][C:40]1([OH:47])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)=[O:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-chloro-5-(2H-[1,2,3]triazol-4-yl)-benzoic acid (0.03 g, 0.136 mmol) in DMF (1.0 mL) was added 1-hydroxybenzotriazole (28 mg, 0.204 mmol), polystyrene supported 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.4 g, 0.4 mmol) and 1-aminomethyl-cycloheptanol hydrochloride (0.036 g, 0.204 mmol). The mixture was stirred at room temperature for 10 minutes, then polystyrene supported N,N-dimethylaminopyridine (0.2 g, 0.29 mmol) was added and the mixture was shaken at room temperature for 16 h. MP-carbonate was added (200 mg) and the mixture was shaken at room temperature for 3 h. The mixture was filtered and washed with methanol. the filtrate was concentrated in vacuo and purified by reverse phase chromatography to afford the title compound (22 mg). LCMS (m/z) 349.3 M+1.
Workup
- additionwas added
- stirringthe mixture was shaken at room temperature for 16 h
- stirringthe mixture was shaken at room temperature for 3 h
- filtrationThe mixture was filtered
- washwashed with methanol
- concentrationthe filtrate was concentrated in vacuo
- custompurified by reverse phase chromatography
Sources & evidence
- ORD record
- ord-0714c97dfbf340f587ae19b0328817af
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553972B2
Reaction notes
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