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

HRID 494287

反応式

HRID 494287 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
38 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-14027445796e482cb578d89752b33991
出典データセット
uspto-grants-2009_05
特許番号
US07538121B2

関連ノート

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