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

HRID 494220

Reaction equation

HRID 494220 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][N:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[C:17]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][CH:18]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:15][N:14]([CH3:16])[CH2:13][CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:18][CH:19]=3)=[O:24])[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 283433417-Amino-1-(2-dimethylaminoethyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 44415475N-[1-(2-Dimethylaminoethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-4-biphenyl-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-1-(2-dimethylaminoethyl)-1,2,3,4-tetrahydroquinoline (D14) (38 mg, 0.152 mmol) in DCM (1 ml) was added 4-biphenylcarboxylic acid (45 mg, 0.22 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (42 mg, 0.22 mmol) and 4-dimethylaminopyridine (2.8 mg, 0.022 mmol) and the reaction stirred at ambient temperature overnight. The crude reaction mixture was loaded directly onto a silica SPE column and elution with EtOAc followed by 1% triethylamine/EtOAc gave the title compound as a red gum. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.94 (d, 2H), 7.75 (br, 1H), 7.70 (d, 2H), 7.64 (d, 2H), 7.47 (t, 2H), 7.39 (t, 1H), 7.01 (d, 1H), 6.92 (d, 1H), 6.82 (dd, 1H), 3.43 (m, 2H), 3.33 (m, 2H), 2.73 (t, 2H), 2.55 (m, 2H), 2.33 (s, 6H), 1.95 (m, 2H).

Workup

  1. customThe crude reaction mixture
  2. washwas loaded directly onto a silica SPE column and elution with EtOAc

Sources & evidence

ORD record
ord-abccb125abfa436f9097c4146c4e0fd2
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Linked notes

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