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

반응식

HRID 452506 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4cc349e7436d458594b944e1ca83bb4f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492311B2

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