Hydrochloric Acid → 4-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-2,5-difluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46238

반응식

HRID 46238 반응식
COC1C=C(OC)C=CC=1C[N:6]([C:19]1[S:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].[NH2:30][C:31]1[CH:36]=[C:35]([C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[OH:44])[CH:34]=[CH:33][N:32]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.Cl>CS(C)=O.ClCCl.C(OCC)(=O)C>[NH2:30][C:31]1[CH:36]=[C:35]([C:37]2[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=2[O:44][C:13]2[C:14]([F:16])=[CH:15][C:10]([S:7]([NH:6][C:19]3[S:23][N:22]=[CH:21][N:20]=3)(=[O:8])=[O:9])=[C:11]([F:18])[CH:12]=2)[CH:34]=[CH:33][N:32]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 1360636192-(2-Aminopyridin-4-yl)-4-chlorophenol

생성물 1

HCID 468408184-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-2,5-difluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

실험 절차

A suspension of N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 647, 10 g, 22.45 mmol), 2-(2-aminopyridin-4-yl)-4-chlorophenol (Preparation 258, 5 g, 22.67 mmol) and potassium carbonate (3.72 g, 26.94 mmol) in dimethyl sulfoxide (150 mL) was stirred at room temperature for 2 hours. The reaction was partitioned between ethyl acetate (150 mL) and saturated aqueous sodium chloride solution (150 mL). The organic layer was collected and concentrated in vacuo to afford an orange residue. This was dissolved in dichloromethane (145 mL) and trifluoroacetic acid (8.48 mL) was added. The reaction was stirred at room temperature for 24 hours before concentrating in vacuo to afford a pink residue. This was taken up in ethyl acetate (200 mL) to form a white slurry that was washed with saturated sodium bicarbonate solution (200 mL). Filtration yielded a white solid that was dried in vacuo, slurried in water and hydrochloric acid (1 N aqueous solution, 1.05 eq) and extracted with ethyl acetate. The organic layer was collected and concentrated in vacuo to yield the title compound.

후처리

  1. customThe reaction was partitioned between ethyl acetate (150 mL) and saturated aqueous sodium chloride solution (150 mL)
  2. customThe organic layer was collected
  3. concentrationconcentrated in vacuo
  4. customto afford an orange residue
  5. stirringThe reaction was stirred at room temperature for 24 hours
  6. concentrationbefore concentrating in vacuo
  7. customto afford a pink residue
  8. customto form a white slurry that
  9. washwas washed with saturated sodium bicarbonate solution (200 mL)
  10. filtrationFiltration
  11. customyielded a white solid
  12. customthat was dried in vacuo
  13. customThe organic layer was collected
  14. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0f36664a25fa4b9498e79fb75cc7417a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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