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 386123ノート

反応式

HRID 386123 の反応式
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

参加物

5

反応物 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、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-16802d7c304247d2b6e045e626af355d
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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