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Ammonium Chloride → N4-[5-Chloro-4-(1-methylindol-3-yl)pyrimidin-2-yl]-N1-(2-dimethylaminoethyl)-5-methoxy-N1-methylbenzene-1,2,4-triamine

HRID 1842751
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HRID 1842751 반응식
[Cl:1][C:2]1[C:3]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH3:36])[CH:28]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([N:18]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH3:19])=[CH:11][C:10]=2[O:25][CH3:26])=[N:6][CH:7]=1.[NH4+].[Cl-]>C(O)C.O.C(OCC)C.[Fe]>[Cl:1][C:2]1[C:3]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH3:36])[CH:28]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([N:18]([CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])[CH3:19])=[CH:11][C:10]=2[O:25][CH3:26])=[N:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 25517Ammonium ChlorideHCID 71269802N-[5-Chloro-4-(1-methylindol-3-yl)pyrimidin-2-yl]-N'-(2-dimethylaminoethyl)-2-methoxy-N'-methyl-5-nitrobenzene-1,4-diamine2회

생성물 1

HCID 86677266N4-[5-Chloro-4-(1-methylindol-3-yl)pyrimidin-2-yl]-N1-(2-dimethylaminoethyl)-5-methoxy-N1-methylbenzene-1,2,4-triamine수율 79%

시약·촉매·용매 4

HCID 23925Iron촉매
HCID 702
Ethanol
용매
HCID 962Water용매
HCID 3283Diethyl Ether용매

실험 절차

A mixture of N-[5-chloro-4-(1-methylindol-3-yl)pyrimidin-2-yl]-N′-(2-dimethylamino-ethyl)-2-methoxy-N′-methyl-5-nitrobenzene-1,4-diamine (Intermediate 98, 553 mg, 1.08 mmol), iron (363 mg, 6.51 mmol) and NH4Cl (43.5 mg, 0.81 mmol) in ethanol (23 mL) and water (7.67 mL) were heated at reflux for 1.5 h. The mixture was then cooled and concentrated in vacuo. The resulting residue was dissolved in CH2Cl2 (100 mL) and CH3OH (10 mL) and this mixture was stirred for 0.25 h and then filtered. The filter cake was washed with further CH2Cl2 and CH3OH and the combined organics were dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-5% methanolic ammonia in CH2Cl2 provided a solid. This solid was dissolved in diethyl ether and a small amount of brown precipitate was removed by filtration. The filtrate was concentrated in vacuo to give the title compound (409 mg, 79%) as a brown glass; 1H NMR: (CDCl3) 2.26 (6H, s), 2.38-2.43 (2H, m), 2.68 (3H, s), 2.94-2.98 (2H, m), 3.84 (3H, s), 3.91 (3H, s), 6.71 (1H, s), 7.26-7.36 (2H, m), 7.40 (1H, d), 7.63 (1H, s), 8.09 (1H, s), 8.21 (1H, s), 8.33 (1H, s), 8.67 (1H, d); m/z: ES+ MH+ 480.32.

후처리

  1. temperaturewere heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in CH2Cl2 (100 mL)
  6. filtrationfiltered
  7. washThe filter cake was washed with further CH2Cl2 and CH3OH
  8. dry with materialthe combined organics were dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification by FCC
  11. washeluting with 0-5% methanolic ammonia in CH2Cl2
  12. customprovided a solid
  13. customa small amount of brown precipitate was removed by filtration
  14. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-df1c947575bf42e1af755a227a5a1abc
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946235B2

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