Sodium Hydroxide → N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

HRID 494212

반응식

HRID 494212 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2C(=O)C(F)(F)F)=[CH:4][CH:3]=1.[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOC(C)=O>[NH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:24]([C:21]3[CH:22]=[CH:23][C:18]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:19][CH:20]=3)=[O:25])[CH:11]=2)[CH2:6][CH2:7][CH2:8]1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 820484221-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

생성물 1

HCID 44415452N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-amino-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D5) (1.17 g, 4.78 mmol) in DCM (20 ml) was added 4-biphenylcarboxylic acid (1.14 g, 5.73 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.06 g, 5.73 mmol) and 4-dimethylaminopyridine (70 mg, 0.57 mmol) and the reaction stirred at room temperature. After 3.75 h the reaction mixture was treated with 2M sodium hydroxide solution overnight. An acid/base work-up followed by flash column chromatography with an EtOAc/60-80° C. petroleum ether gradient gave the title compound as a beige solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.91 (d, 2H), 7.63 (m, 5H), 7.47 (t, 2H), 7.41 (t, 1H), 7.11 (d, 1H), 6.91 (d, 1H), 6.61 (dd, 1H), 3.94 (br, 1H), 3.31 (m, 2H), 2.74 (t, 2H), 1.93 (m, 2H), 1.57 (br, 2H).

출처 및 근거

ORD 기록
ord-f20150feb6a0428db66835c8cb89843d
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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