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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(5-Chloroquinolin-7-yl)-6-(4-Fluorophenyl)-2-ethyl-nicotinamide

HRID 494277
ノート
印刷プレビュー

反応式

HRID 494277 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([Cl:12])[CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22]([CH3:29])[N:21]=2)=[CH:16][CH:15]=1.Cl.[CH3:31]N(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:12][C:4]1[CH:3]=[C:2]([NH:1][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][C:20]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)=[N:21][C:22]=2[CH2:29][CH3:31])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 242777906-(4-Fluorophenyl)-2-methylpyridine-3-carboxylic acidHCID 690423405-Chloroquinolin-7-amine

生成物 1

HCID 86760866N-(5-Chloroquinolin-7-yl)-6-(4-Fluorophenyl)-2-ethyl-nicotinamide

試薬・触媒・溶媒 2

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

実験手順

To a solution of 7-amino-5-chloroquinoline (D83) (50 mg, 0.28 mmol) in DCM (3 ml) was added 6-(4-fluorophenyl)-2-methyl-nicotinic acid (D24) (30 mg, 0.13 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (59 mg, 0.31 mmol) and 4-dimethylaminopyridine (17 mg, 0.14 mmol) and the reaction stirred at room temperature then at reflux until complete by tlc. The mixture was washed with sat. aq. sodium bicarbonate solution then dried over MgSO4 and concentrated to give the crude product. Purification by SPE column chromatography gave the title compound as an off white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.94 (dd, 1H), 8.54 (d, 1H), 8.29 (s, 1H), 8.05 (m, 3H), 7.92 (d, 1H), 7.78 (br.s, 1H), 7.62 (d, 1H), 7.47 (dd, 1H), 7.18 (t, 2H), 2.84 (s, 3H).

後処理

  1. temperatureat reflux until complete by tlc
  2. washThe mixture was washed with sat. aq. sodium bicarbonate solution
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by SPE column chromatography

出典と根拠

ORDレコード
ord-3683c93bc55f416698da9a4ce408167f
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07538121B2

反応ノート

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