2,4-Dichloro-5-methoxyaniline → N-[3-cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl]acetamide

HRID 396187

反応式

HRID 396187 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:14][C:15](=[O:17])[CH3:16])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Cl:20][C:21]1[CH:27]=[C:26]([Cl:28])[C:25]([O:29][CH3:30])=[CH:24][C:22]=1[NH2:23].Cl.N1C=CC=CC=1>C(OCCO)C>[C:18]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:23][C:22]1[CH:24]=[C:25]([O:29][CH3:30])[C:26]([Cl:28])=[CH:27][C:21]=1[Cl:20])=[CH:10][C:9]([O:12][CH3:13])=[C:8]([NH:14][C:15](=[O:17])[CH3:16])[CH:7]=2)#[N:19]

参加物

5

反応物 3

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 10176127Pyridinium chlorideHCID 23438009N-(4-chloro-3-cyano-6-methoxy-7-quinolinyl)acetamide

生成物 1

HCID 23438166N-[3-cyano-4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-quinolinyl]acetamide収率 71%

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

反応条件

温度
135 °C

実験手順

An amount of 9.7 g (0.035 mol) of N-(4-chloro-3-cyano-6-methoxy-7-quinolinyl)acetamide was stirred in 97 ml of 2-ethoxyethanol. To this were added 2,4-dichloro-5-methoxyaniline (7.4 g, 0.038 mol), and 4.1 g (0.035 mol) pyridine hydrochloride, and the mixture was heated at 135° C. for 3 hours. The solvent was evaporated and the solid was stirred in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with saturated brine solution, dried over sodium sulfate and evaporated to dryness to give a brown solid (10.7 g, 71% yield), mp 267-270° C.; 1H NMR (DMSO-d6) δ 9.94 (s, 1H), 9.01 (s, 1H), 8.99 (s, 1H), 8.42 (s, 1H), 7.97 (m, 1H), 7.86 (s, 1H), 7.53 (m, 1H), 4.12 (s, 3H), 3.88 (s, 3H), 2.27 (s, 3H); MS (ES) m/z 431.1 (M+1). Analysis for C20H16Cl2N4O3.7H2O: Found: C, 43.23; H, 3.35; N, 10.24. Calcd: C, 43.06; H, 5.38; N, 10.05.

後処理

  1. customThe solvent was evaporated
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with saturated brine solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-97b741e4a85344d68def515d5aa2f45b
出典データセット
uspto-grants-2003_08
特許番号
US06608048B2

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