Ethanol → 4-{2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyrimidin-4-ylbenzenesulfonamide

HRID 1402070ノート

反応式

HRID 1402070 の反応式
[Cl:1][C:2]1[C:3]([O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[C:30]2[C:31]([N+:41]([O-])=O)=[N:32][N:33]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH:34]=2)=[CH:4][C:5]([F:21])=[C:6]([S:8]([N:11]([CH2:18][O:19][CH3:20])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.C(O)C.[Cl-].[NH4+]>[Fe]>[NH2:41][C:31]1[C:30]([C:24]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=2[O:22][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([N:11]([CH2:18][O:19][CH3:20])[C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])=[C:5]([F:21])[CH:4]=2)=[CH:34][N:33]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[N:32]=1

参加物

5

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 594365105-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide

生成物 1

HCID 594365744-{2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyrimidin-4-ylbenzenesulfonamide収率 97.8%

試薬・触媒・溶媒 1

HCID 23925Iron触媒

反応条件

温度
80 °C

実験手順

To a solution of 5-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide (80 mg, 0.1 mmol) in ethanol (4 mL, 70 mmol) was added saturated aqueous ammonium chloride solution (0.4 mL, 6 mmol) and iron (328 mg, 5.87 mmol). The reaction solution was heated at 80° C. for 20 minutes then filtered. Saturated aqueous sodium bicarbonate was added until the pH was 9. The mixture was concentrated in vacuo to remove the ethanol. Water was added and the mixture was extracted three times with dichloromethane. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified on silica gel (hexane to 100% ethyl acetate gradient) to give 61 mg of a colorless oil.

後処理

  1. filtrationthen filtered
  2. additionSaturated aqueous sodium bicarbonate was added until the pH was 9
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove the ethanol
  5. additionWater was added
  6. extractionthe mixture was extracted three times with dichloromethane
  7. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on silica gel (hexane to 100% ethyl acetate gradient)

出典と根拠

ORDレコード
ord-9106f9b4145f4ebe9a40c31f40c46b8f
出典データセット
uspto-grants-2014_12
特許番号
US08907101B2

反応ノート

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