Triethylamine → 7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-methoxypropan-2-yl)-3-nitroquinolin-4-amine

HRID 81986

Reaction equation

HRID 81986 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH2:6])[CH3:5].Cl[C:8]1[C:17]2[C:12](=[CH:13][C:14]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][C:9]=1[N+:27]([O-:29])=[O:28].C(N(CC)CC)C>CN1C(=O)CCC1.O>[CH3:26][C:21]1[C:20]([C:14]2[CH:13]=[C:12]3[C:17]([C:8]([NH:6][CH:4]([CH3:5])[CH2:3][O:2][CH3:1])=[C:9]([N+:27]([O-:29])=[O:28])[CH:10]=[N:11]3)=[CH:16][C:15]=2[O:18][CH3:19])=[C:24]([CH3:25])[O:23][N:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123458MethoxyisopropylamineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole

Product 1

HCID 709805047-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-methoxypropan-2-yl)-3-nitroquinolin-4-amineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(Methyloxy)-2-propanamine (0.35 g) and 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitroquinoline (for a preparation see Intermediate 8) (0.74 g, 2.217 mmol) were dissolved in a mixture of triethylamine (0.30 ml, 2.2 mmol) and NMP (3 ml) and the solution was allowed to stand for 30 min at room temperature, then diluted with water (20 ml) and the resulting suspension stirred for 20 min, then filtered and the resulting solid washed with water (10 ml) and dried in the vacuum oven at 50° C. to give the title compound as bright yellow solid. (0.80 g, 2.070 mmol, 93% yield). LCMS (formate) Rt 0.97 MH+ 387

Workup

  1. filtrationfiltered
  2. washthe resulting solid washed with water (10 ml)
  3. customdried in the vacuum oven at 50° C.

Sources & evidence

ORD record
ord-f38cf3b8a8294bdb8d82abf63fdbd1ec
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Linked notes

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