Dimethylformamide → 4-(tert-butyl)-N-[3-{2-[(5-formyl-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1368592노트

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HRID 1368592 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:15]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[N:14]([CH3:38])[N:13]=2)=[N:6][CH:7]=1.C([Li])CCC.CN(C)[CH:46]=[O:47]>O1CCCC1>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([S:25]([NH:24][C:15]2[N:14]([CH3:38])[N:13]=[C:12]([O:11][CH2:10][CH2:9][O:8][C:5]3[N:4]=[CH:3][C:2]([CH:46]=[O:47])=[CH:7][N:6]=3)[C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:27])=[O:26])=[CH:29][CH:30]=1)([CH3:37])([CH3:36])[CH3:35]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 9894949N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamideHCID 178418339Butyllithium

생성물 1

HCID 222819404-(tert-butyl)-N-[3-{2-[(5-formyl-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 3) (332 mg) in tetrahydrofuran (10 ml) at −78° C. under an atmosphere of nitrogen was added n-butyllithium in hexanes (0.69 ml of 1.6M). Dimethylformamide (86 μl) was added dropwise to the solution after 20 minutes of stirring at −78° C. After a further 20 minutes of stirring at −78° C., the mixture was quenched with saturated ammonium chloride solution (2 ml). The mixture was diluted with ammonium chloride (50 ml), extracted with ethyl acetate (50 ml), dried over magnesium sulphate, filtered and the filtrate was evaporated to dryness. Purification of the residue by column chromatography on silica gel (32 g), eluting with an ethyl acetate:hexane gradient (1:1 to 3:1) yielded the title compound as a cream solid (52 mg).

후처리

  1. stirringAfter a further 20 minutes of stirring at −78° C.
  2. customthe mixture was quenched with saturated ammonium chloride solution (2 ml)
  3. additionThe mixture was diluted with ammonium chloride (50 ml)
  4. extractionextracted with ethyl acetate (50 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness
  8. customPurification of the residue by column chromatography on silica gel (32 g)
  9. washeluting with an ethyl acetate

출처 및 근거

ORD 기록
ord-822dade28e674ded94cf5701e3bc11e6
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573270B1

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