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

HRID 396187

반응식

HRID 396187 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8076Glycol monoethyl ether용매

반응 조건

온도
135 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-97b741e4a85344d68def515d5aa2f45b
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608048B2

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