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

HRID 1043004Notes

Reaction equation

HRID 1043004 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-379f8e894db24296a3b8a5fa6de810b5
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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