Reaction equation
CCN=C=NCCCN(C)C.[CH2:12]([N:14]1[C:18]([C:19]2[CH:20]=[C:21]([C:32](O)=[O:33])[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[CH:24]=2)=[N:17][N:16]=[N:15]1)[CH3:13].C1C=CC2N(O)N=NC=2C=1.CN1C(=O)CCC1.[CH3:52][O:53][CH2:54][CH:55]([NH2:57])[CH3:56]>C(Cl)Cl>[CH3:52][O:53][CH2:54][CH:55]([NH:57][C:32]([C:21]1[CH:22]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[CH:24]=[C:19]([C:18]2[N:14]([CH2:12][CH3:13])[N:15]=[N:16][N:17]=2)[CH:20]=1)=[O:33])[CH3:56]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
EDCI (54.0 mg, 0.282 mmol) was added in one portion to a solution of 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid (70.0 mg, 0.229 mmol), HOBt (40.0 mg, 0.296 mmol) and NMP (101.5 mg, 1.000 mmol) in CH2Cl2 (5 mL) at 0° C. After the reaction stirred at the same temperature for 1 hour, 2-methoxy-1-methyl-ethylamine (64.3 mg, 0.72 mmol) was added. The mixture was allowed to warm to room temperature and was stirred overnight. Solvent was removed under reduced pressure and the residue was purified by column chromatography to afford 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as white solid (40 mg, 46%). MS (M+H)=380.
Workup
- stirringwas stirred overnight
- customSolvent was removed under reduced pressure
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-89c9e1d10fa64019a3fa785d5bc07684
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841336B2
Linked notes
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