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Potassium Hydroxide → Propane-1-sulfonic acid{2,4-difluoro-3-[hydroxy-(4-methyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide

HRID 1690034
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HRID 1690034 반응식
[CH3:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N: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][CH2:26][CH3:27])(=[O:24])=[O:23].[OH-].[K+]>CO>[F:11][C:12]1[C:17]([CH:18]([OH:19])[C:10]2[C:3]3[C:2]([CH3:1])=[N:7][CH:6]=[N:5][C:4]=3[NH:8][CH:9]=2)=[C:16]([F:20])[CH:15]=[CH:14][C:13]=1[NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23]
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참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 513419594-Methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamide

생성물 1

HCID 57963260Propane-1-sulfonic acid{2,4-difluoro-3-[hydroxy-(4-methyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide수율 37.7%

시약·촉매·용매 1

HCID 887Methanol
용매

실험 절차

To 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (42, 0.192 g, 1.44 mmol), propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (9, 0.456 g, 1.73 mmol), potassium hydroxide (0.263 g, 4.69 mmol) and 1.0 mL of methanol were added to provide a solution. The reaction was allowed to stir at room temperature for 30 hours, then quenched with water and adjusted to pH ˜5 with acetic acid and sodium bicarbonate and extracted with ethyl acetate and saturated sodium chloride. The organic layer was washed with water and brine, dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane with 4% acetic acid. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as an off-white solid (P-0055, 215 mg). 1H-NMR(dmso-d6) showed it contains about >80% of the desired compound, used in the next step without further purification. MS(ESI) [M+H−]+=397.1.

후처리

  1. customto provide a solution
  2. customquenched with water
  3. extractionextracted with ethyl acetate and saturated sodium chloride
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with ethyl acetate and hexane with 4% acetic acid
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-2d09969b84dc4fde8a32038368aa8d10
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153641B2

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