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

HRID 548496

反応式

HRID 548496 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5dcf653adbc4474b9992b3bb174d029d
出典データセット
uspto-grants-2011_05
特許番号
USRE042376E1

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