(1,1'-Biphenyl)-4-carboxylic acid → N-(1-Methyl-1,2,3,4-tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide
Reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[C:13]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:14][CH:15]=3)=[O:20])[CH:11]=2)[CH2:6][CH2:7][CH2:8]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7-amino-1-methyl-1,2,3,4-tetrahydroquinoline (D3) (325 mg, 2 mmol) in DCM (10 ml) was added 4-biphenylcarboxylic acid (476 mg, 2.4 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (444 mg, 2.4 mmol) and the reaction stirred at ambient temperature. After 1 h the reaction mixture was filtered to give the title compound as a white solid. The filtrate was diluted with DCM, washed with sat. aq. sodium bicarbonate solution, dried over MgSO4 and concentrated in vacuo to give further crude product which was purified by silica SPE chromatography. Elution with an EtOAc/60-80° C. petroleum ether gradient gave a mixture of the title compound and the starting acid. These fractions were washed with further sat. aq. sodium bicarbonate solution, dried over MgSO4 and concentrated in vacuo to give further title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.94 (d, 2H), 7.70 (m, 3H), 7.63 (d, 2H), 7.48 (t, 2H), 7.40 (t, 1H), 7.07 (d, 1H), 6.93 (d, 1H), 6.75 (dd, 1H), 3.25 (m, 2H), 2.94 (s, 3H), 2.76 (t, 2H), 1.98 (m, 2H).
Workup
- filtrationAfter 1 h the reaction mixture was filtered
Sources & evidence
- ORD record
- ord-ecde2c0ceed1427d95547943e35ffba2
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538121B2
Reaction notes
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