Sulfuric Acid → 6-(4-Chlorobutylamino)-4-(3-chloro-4-fluorophenyamino)-7-methoxy-3-quinolinecarbonitrile

HRID 379193

Reaction equation

HRID 379193 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]=O.S(=O)(=O)(O)O.[NH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][C:17]([C:25]#[N:26])=[C:16]2[NH:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[C:30]([Cl:35])[CH:29]=1.[BH4-].[Na+]>O1CCCC1.CN(C)C=O.O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][C:17]([C:25]#[N:26])=[C:16]2[NH:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[C:30]([Cl:35])[CH:29]=1

Participants

8

Reactant 4

HCID 1118Sulfuric Acid2×HCID 2422004-ChlorobutanalHCID 4311764Sodium borohydride2×HCID 111424366-Amino-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinoline-3-carbonitrile

Product 1

HCID 672046396-(4-Chlorobutylamino)-4-(3-chloro-4-fluorophenyamino)-7-methoxy-3-quinolinecarbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.12 g of 4-chlorobutanal and 5.3 ml of 3M sulfuric acid in 11 ml of tetrahydrofuran, at 0° C., was added an solution of 2.0 g of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-3-quinolinecarbonitrile in 40 ml of dimethylforamide. To this was added portionwise 0.4 g of sodium borohydride. After 1 hr another 1.0 g of aldehyde, 10 ml of dimethylforamide, and 5 ml of 3M sulfuric acid was added followed by the portionwise addition of 0.8 g of sodium borohydride. After 2 hrs, the mixture was poured into water and the Ph was adjusted to 9. The mixture was extracted with ethyl acetate several times. The organic solution was dried over magnesium sulfate and the solvent was removed giving the title compound as an oil which was used without additional purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate several times
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-878c64689f1645daa3069f67bee9fdf1
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Linked notes

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