(1,1'-Biphenyl)-4-carboxylic acid → N-(Isoquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

HRID 494290Notes

Reaction equation

HRID 494290 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:12]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][C:15]([C:18](O)=[O:19])=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:13][CH:14]=3)=[O:19])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14660277Isoquinolin-7-amine

Product 1

HCID 44415608N-(Isoquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-aminoisoquinoline (D96) (88 mg, 0.61 mmol) in DCM (4 ml) was added 4-biphenylcarboxylic acid (145 mg, 0.73 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (140 mg, 0.73 mmol) and the reaction stirred at ambient temperature overnight. The reaction mixture was filtered to give the title compound as a white solid. The filtrate was diluted with DCM, washed with 2M sodium hydroxide 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 further title compound which was combined with the sample obtained from the filtration. This was dissolved in ethanol and treated with ethereal HCl and the resultant precipitate was collected to give the HCl salt of the title compound as a white solid. 1H NMR (250 MHz, DMSO) δ (ppm): 9.80 (s, 1H), 9.09 (d, 1H), 8.58 (d, 1H), 8.40 (dd, 1H), 8.33 (d, 1H), 8.28 (d, 1H), 8.16 (d, 2H), 7.90 (d, 2H), 7.79 (d, 2H), 7.54 (t, 2H), 7.45 (t, 1H)

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-b256173174874af7bd633c19235567e8
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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