Sodium Bicarbonate → 5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(1H-pyrazol-5-yl)pyridazin-3-yl]amino}thiophene-3-carboxamide

HRID 386123노트

반응식

HRID 386123 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[S:10][C:11]([C:17]3[C:22]([F:23])=[CH:21][C:20]([C:24]([OH:27])([CH3:26])[CH3:25])=[CH:19][C:18]=3[F:28])=[CH:12][C:13]=2[C:14]([NH2:16])=[O:15])=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[CH:32][C:31](B(O)O)=[N:30]1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:28][C:18]1[CH:19]=[C:20]([C:24]([OH:27])([CH3:26])[CH3:25])[CH:21]=[C:22]([F:23])[C:17]=1[C:11]1[S:10][C:9]([NH:8][C:5]2[N:6]=[N:7][C:2]([C:31]3[NH:30][N:29]=[CH:33][CH:32]=3)=[CH:3][CH:4]=2)=[C:13]([C:14]([NH2:16])=[O:15])[CH:12]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 595261282-[(6-Chloropyridazin-3-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamideHCID 178514837HCID 178514837, 화합물

생성물 1

HCID 595262175-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(1H-pyrazol-5-yl)pyridazin-3-yl]amino}thiophene-3-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-[(6-chloropyridazin-3-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (64 mg, 0.15 mmol) in THF (3 ml), was added 1H-pyrazol-3-yl boronic acid (34 mg, 0.30 mmol), and sodium bicarbonate (0.38 ml, 0.75 mmol, 2 M). Palladium tetrakis triphenylphosphine (35 mg, 0.03 mmol) was added last and the vial was purged with nitrogen for 5 minutes. The crude product was washed with 3:1 chloroform:isopropanol and water. The resulting organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Purification by column chromatography yielded the title compound.

후처리

  1. customthe vial was purged with nitrogen for 5 minutes
  2. washThe crude product was washed with 3:1 chloroform
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-16802d7c304247d2b6e045e626af355d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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