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(Dimethyl-1,3-thiazol-5-yl)methanamine → 7-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine

HRID 1043003
Notes
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Reaction equation

HRID 1043003 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH3:24][C:25]1[S:26][C:27]([CH2:31][NH2:32])=[C:28]([CH3:30])[N:29]=1>C(#N)C.O>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][CH2:31][C:27]4[S:26][C:25]([CH3:24])=[N:29][C:28]=4[CH3:30])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 25219195(Dimethyl-1,3-thiazol-5-yl)methanamineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole2×

Product 1

HCID 672080477-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitroquinoline (for a preparation see Intermediate 18, 1.5 g) in acetonitrile was added [(2,4-dimethyl-1,3-thiazol-5-yl)methyl]amine (1.6 g) and the resulting mixture was stirred overnight at 80° C. Another portion of amine (0.64 g) was added and the mixture was stirred at 80° C. for 6 h. The reaction mixture was diluted with water, extracted with DCM and the organic phase were dried over Na2SO4, and concentrated to dryness to give a dark red oil. The residue was purified by flash chromatography on silica gel, eluting with DCM/methanol (99:1 then 95:5) to give 7-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine (1.13 g) as an orange oil.

Workup

  1. stirringthe mixture was stirred at 80° C. for 6 h
  2. extractionextracted with DCM
  3. dry with materialthe organic phase were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customto give a dark red oil
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with DCM/methanol (99:1

Sources & evidence

ORD record
ord-78fed5b6334b4d09a77e76328fbff820
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes