(1,1'-Biphenyl)-4-carboxylic acid → N-(1-Methylisoquinolin-5-yl)-1,1'-biphenyl-4-carboxamide

HRID 494287

반응식

HRID 494287 반응식
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N: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.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([NH:12][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:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99894901-Methylisoquinolin-5-amine

생성물 1

HCID 57682685N-(1-Methylisoquinolin-5-yl)-1,1'-biphenyl-4-carboxamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
38 °C

실험 절차

To a solution of 1-methyl-5-aminoisoquinoline (94 (75 mg, 0.47 mmol) in DCM (4 ml) was added 4-biphenylcarboxylic acid (141 mg, 0.71 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (135 mg, 0.71 mmol) and 4-dimethylaminopyridine (10 mg, 0.08 mmol) and the reaction stirred at 38° C. for 3 days. The mixture was diluted with DCM, washed with sat. aqueous sodium bicarbonate solution and water, dried over MgSO4 and concentrated in vacuo to give the crude product which was triturated with methanol. The resulting precipitate was collected by filtration, washed with ether and dried in vacuo giving the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.48 (d, 1H), 8.33 (d, 1H), 8.21 (br, 1H), 8.06 (m, 3H), 7.78 (d, 2H), 7.68 (m, 3H), 7.58 (d, 1H), 7.51 (t, 2H), 7.41 (t, 1H), 3.02 (s, 3H).

후처리

  1. washwashed with sat. aqueous sodium bicarbonate solution and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product which
  5. customwas triturated with methanol
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with ether
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-14027445796e482cb578d89752b33991
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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