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Hydrochloric Acid → 7-(3,5-dimethyl-4-isoxazolyl)-N4-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3,4-quinolinediamine

HRID 1043004
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HRID 1043004 반응식
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][C:22]4[S:26][C:25]([CH3:27])=[N:24][C:23]=4[CH3:28])=[C:12]([N+:17]([O-])=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1.Cl.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][C:22]4[S:26][C:25]([CH3:27])=[N:24][C:23]=4[CH3:28])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 672080477-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine

생성물 1

HCID 672075147-(3,5-dimethyl-4-isoxazolyl)-N4-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3,4-quinolinediamine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine (for a preparation see intermediate 69, 1.13 g) in ethanol was added hydrochloric acid (2 ml, conc). Tin (II) chloride dihydrate (2.32 g) was added and the mixture was stirred at 40° C. for 1 h. The reaction mixture was cooled, diluted with water and basified using sodium hydroxide solution (1N). The formed precipitate was filtered through Celite and rinsed with DCM. The filtrate was washed with water and the organic was dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with DCM/methanol (98:2 then 93:7) to give 7-(3,5-dimethyl-4-isoxazolyl)-N4-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3,4-quinolinediamine (0.6 g) as a beige foam.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe formed precipitate was filtered through Celite
  3. washrinsed with DCM
  4. washThe filtrate was washed with water
  5. dry with materialthe organic was dried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica gel eluting with DCM/methanol (98:2

출처 및 근거

ORD 기록
ord-379f8e894db24296a3b8a5fa6de810b5
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08557984B2

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