HCID 67208015, compound → 7-(3,5-dimethyl-4-isoxazolyl)-N4-(phenylmethyl)-3,4-quinolinediamine

HRID 1042985Notes

Reaction equation

HRID 1042985 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=C[C:6]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([C:22]3[C:23]([CH3:28])=[N:24][O:25][C:26]=3[CH3:27])=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[N+:29]([O-])=O)(C)(C)[CH3:2]>C(O)C.C1COCC1>[CH3:28][C:23]1[C:22]([C:18]2[CH:17]=[C:16]3[C:21]([C:12]([NH:11][CH2:6][C:5]4[CH:1]=[CH:2][CH:8]=[CH:9][CH:10]=4)=[C:13]([NH2:29])[CH:14]=[N:15]3)=[CH:20][CH:19]=2)=[C:26]([CH3:27])[O:25][N:24]=1

Participants

4

Reactant 1

HCID 67208015HCID 67208015, compound2×

Product 1

HCID 672063207-(3,5-dimethyl-4-isoxazolyl)-N4-(phenylmethyl)-3,4-quinolinediamineYield 100.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-(tert-butyl)phenyl]-7-(3,5-dimethyl-4-isoxazolyl)-3-nitro-4-quinolinamine (see Intermediate 19, 2.4 g, 5.77 mmol) in a mixture of ethanol (60 ml) and THF (20 ml), was added SnCl2,2H2O (7.81 g, 34.6 mmol). The reaction mixture was refluxed for 3 h and then concentrated to dryness. The resulting residue was poured into aqueous sodium hydroxide. The organic phase was extracted with EtOAc, washed with water, dried and concentrated to give the title compound as a yellow solid (2 g, 71%). [APCI-MS] m/z: 387 MH+, Rt 3.37 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. concentrationconcentrated to dryness
  3. additionThe resulting residue was poured into aqueous sodium hydroxide
  4. extractionThe organic phase was extracted with EtOAc
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-62fe508c153e48e19212cdace83a1714
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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