Sodium Chloride → 2-methyl-propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide

HRID 217617노트

반응식

HRID 217617 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:11][C:12]1[C:17]([CH:18]=[O:19])=[C:16]([F:20])[CH:15]=[CH:14][C:13]=1[NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23].[OH-].[K+].[Cl-].[Na+]>C(OCC)(=O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:18]([OH:19])[C:17]3[C:12]([F:11])=[C:13]([NH:21][S:22]([CH2:25][CH:26]([CH3:27])[CH3:28])(=[O:24])=[O:23])[CH:14]=[CH:15][C:16]=3[F:20])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 583169302-Methyl-propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide

생성물 1

HCID 595695972-methyl-propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide수율 89.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

In a reaction vial, 5-bromo-1H-pyrrolo[2,3-b]pyridine (55, 287 mg, 1.46 mmol), 2-methyl-propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (59, 445 mg, 1.60 mmol) and potassium hydroxide (246 mg, 4.38 mmol) are combined with 7 mL of methanol and stirred at room temperature overnight. The reaction was combined with ethyl acetate and aqueous saturated sodium chloride, and extracted. The organic layer was washed with water, brine, and dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue was treated with 75 mL of acetonitrile:water 4:1 with 5% trifluoroacetic acid and stirred overnight at room temperature. The reaction was combined with ethyl acetate and aqueous saturated sodium chloride, and extracted. The organic layer was washed with water, brine, and dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (68, 618 mg).

후처리

  1. extractionextracted
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. additionThe residue was treated with 75 mL of acetonitrile:water 4:1 with 5% trifluoroacetic acid
  7. stirringstirred overnight at room temperature
  8. extractionextracted
  9. washThe organic layer was washed with water, brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under vacuum

출처 및 근거

ORD 기록
ord-5babb612c47e4960859885557c47db43
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198273B2

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