(1,1'-Biphenyl)-4-carboxylic acid → N-[1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

HRID 494219Notes

Reaction equation

HRID 494219 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[CH2:12][CH2:13][O:14][CH3:15])=[CH:4][CH:3]=1.[C:16]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:15][O:14][CH2:13][CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:22]([C:19]3[CH:20]=[CH:21][C:16]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:17][CH:18]=3)=[O:23])[CH:11]=2)[CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 392414391-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-amine

Product 1

HCID 44415474N-[1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-amino-1-(2-methoxyethyl)-1,2,3,4-tetrahydroquinoline (D13) (72 mg, 0.35 mmol) in DCM (2.5 ml) was added 4-biphenylcarboxylic acid (104 mg, 0.53 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (97 mg, 0.53 mmol) and 4-dimethylaminopyridine (6 mg, 0.05 mmol) and the reaction stirred at ambient temperature overnight. The mixture was diluted with DCM, washed with 2M sodium hydroxide solution, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by silica SPE chromatography. Elution with 20% EtOAc/60-80° C. petroleum ether gave the title compound as a pale yellow solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.93 (d, 2H), 7.77 (br, 1H), 7.69 (d, 2H), 7.62 (d, 2H), 7.47 (t, 2H), 7.39 (t, 1H), 7.06 (d, 1H), 6.91 (d, 1H), 6.73 (dd, 1H), 3.63 (t, 2H), 3.49 (t, 2H), 3.37 (s, 3H), 3.36 (t, 2H), 2.73 (t, 2H), 1.91 (m, 2H).

Workup

  1. washwashed with 2M sodium hydroxide solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product which
  5. customwas purified by silica SPE chromatography
  6. washElution with 20% EtOAc/60-80° C. petroleum ether

Sources & evidence

ORD record
ord-a5875f1f58324870a3a383f7fb097ab4
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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