Formaldehyde → 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl) benzoic acid amide

HRID 452506

反応式

HRID 452506 の反応式
[NH2:1][C:2]1[CH:15]=[C:14]([C:16]2[CH2:20][C:19]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=2)[CH:13]=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][C:8]([F:11])([F:10])[F:9])=[O:5].C=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:32][C:27]1[CH:26]=[C:25]([C:19]2([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=[C:16]([C:14]3[CH:13]=[CH:12][C:3]([C:4]([NH:6][CH2:7][C:8]([F:10])([F:9])[F:11])=[O:5])=[C:2]([NH:1][CH3:35])[CH:15]=3)[CH2:20]2)[CH:30]=[C:29]([Cl:31])[CH:28]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866114682-amino-4-[5-(3,5-dichlorophenyl)-5-trifiuoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifiuoroethyl) benzoic acid amide

生成物 1

HCID 866114744-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl) benzoic acid amide収率 50.6%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

In a solution of 0.25 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-329) synthesized in Synthetic Example 12 and 0.06 g of 36% formaldehyde aqueous solution in 7 ml of 1,2-dichloroethane, 1.00 g of sodium triacetoxy borohydride was added with stirring at room temperature in three portions at 1 hour-interval, and continued to stir at the same temperature for further 2 hours. After the completion of the reaction, the reaction mixture was poured to 5 ml of ice water, the organic phase was collected, and the solvent was distilled under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (0:1 to 1:3 gradient), and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide was obtained as pale yellow crystal, and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide was obtained as pale yellow resinous substance.

後処理

  1. additionwas added
  2. stirringto stir at the same temperature for further 2 hours
  3. customAfter the completion of the reaction
  4. customthe organic phase was collected
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that
  7. washwas eluted with ethyl acetate-hexane (0:1 to 1:3 gradient)

出典と根拠

ORDレコード
ord-4cc349e7436d458594b944e1ca83bb4f
出典データセット
uspto-grants-2013_07
特許番号
US08492311B2

関連ノート

読み込み中…