Hydrochloric Acid → 1-Methyl-4-[4-({4-[(6-nitro-4-quinolinyl)amino]anilino}carbonyl)anilino]pyridinium chloride

HRID 547533노트

반응식

HRID 547533 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl-].[NH2:16][C:17]1[CH:39]=[CH:38][C:20]([NH:21][C:22]([C:24]2[CH:37]=[CH:36][C:27]([NH:28][C:29]3[CH:34]=[CH:33][N+:32]([CH3:35])=[CH:31][CH:30]=3)=[CH:26][CH:25]=2)=[O:23])=[CH:19][CH:18]=1.Cl.CO.CCOC(C)=O>CO.CCOC(C)=O>[Cl-:1].[CH3:35][N+:32]1[CH:31]=[CH:30][C:29]([NH:28][C:27]2[CH:26]=[CH:25][C:24]([C:22]([NH:21][C:20]3[CH:19]=[CH:18][C:17]([NH:16][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=5)[N:5]=[CH:4][CH:3]=4)=[CH:39][CH:38]=3)=[O:23])=[CH:37][CH:36]=2)=[CH:34][CH:33]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 2872104-Chloro-6-nitroquinoline2회HCID 21584119Ethylacetate methanolHCID 672001654-{4-[(4-Aminoanilino)carbonyl]anilino}-1-methylpyridinium chloride

생성물 1

HCID 671997341-Methyl-4-[4-({4-[(6-nitro-4-quinolinyl)amino]anilino}carbonyl)anilino]pyridinium chloride

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

To a suspension of 4-chloro-6-nitroquinoline (70 mg, 0.33 mmol) in MeOH (10 mL) was added compound D5 (100 mg, 0.28 mmol), and the mixture was stirred at 20° C. for 1 h (until a clear solution obtained). A drop of c.HCl was then added, and refluxing was continued for a further 20 h. TLC analysis (eluting with the top phase of a 5:4:1 mixture of n-BuOH:H2O:AcOH) showed some D5 remained, so more 4-chloro-6-nitroquinoline (35 mg, 0.16 mmol) was added and refluxing was continued for a further 4 h. The reaction mixture was then diluted with EtOAc and the resulted precipitate was filtered and washed sequentially with EtOAc, CH2Cl2 and diisopropylether, and finally crystallized from MeOH EtOAc to give Cpd. N1 (111 mg, 75%), mp (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ14.50 (br, 1 H, N+H); 11,42, (br s, 1 H, NH), 11.10 (s, 1 H, NH), 10.58 (s, 1 H, NH), 9.82 (d, J=2.1 Hz, 1 H, ArH), 8.72 (dd, J=9.3, 2.2 Hz, 1 H, ArH), 8.60 (d, J=7.0 Hz, 1 H, ArH), 8.42 (d, J=7.4 Hz, 2 H, ArH), 8.24 (d, J=8.6 Hz, 1 H, ArH), 8.15 (d, J=8.6 Hz, 2 H, ArH), 8.04 (d, J=8.8 Hz, 2 H, ArH), 7.51 (t, J=8.3 Hz, 4 H, ArH), 7.34 (d, J=7.5 Hz, 2 H, ArH), 6.91 (d, J=7.0 Hz, 1 H, ArH), 4.01 (s, 3 H, N+CH3); LCMS 489+ve.

후처리

  1. customobtained)
  2. temperaturerefluxing
  3. waitwas continued for a further 20 h
  4. washTLC analysis (eluting with the top phase of a 5:4:1 mixture of n-BuOH
  5. temperaturerefluxing
  6. waitwas continued for a further 4 h
  7. filtrationthe resulted precipitate was filtered
  8. washwashed sequentially with EtOAc, CH2Cl2 and diisopropylether
  9. customfinally crystallized from MeOH EtOAc
  10. customto give Cpd

출처 및 근거

ORD 기록
ord-6756e6cf50f6455a832c723ebda240e5
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939546B2

반응 노트

불러오는 중…