Water → N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine

HRID 70721ノート

反応式

HRID 70721 の反応式
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3]C1.C(=O)(O)[O-].[Na+].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH:23](Cl)[C:24]2[N:29]=[C:28]([O:30][CH3:31])[C:27]([Cl:32])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].O>C(#N)C>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:24]2[CH:25]=[CH:26][C:27]([Cl:32])=[C:28]([O:30][CH3:31])[N:29]=2)[NH:7][CH:1]2[CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 4

HCID 962WaterHCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 673982706-[(4-Tert-butylphenyl)(chloro)methyl]-3-chloro-2-methoxypyridine

生成物 1

HCID 67399418N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Cyclohexylamine (0.30 mL) and sodium bicarbonate (259 mg) were sequentially added to a solution of 6-[(4-tert-butylphenyl)(chloro)methyl]-3-chloro-2-methoxypyridine (200 mg) in acetonitrile (4 mL) at room temperature, and then the mixture was heated under reflux for six hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:50→1:10) to give N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine as a pale yellow amorphous (201 mg, 87%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for six hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customafter which the solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:50→1:10)

出典と根拠

ORDレコード
ord-c1b699ce134941fbbd8f34758385d5eb
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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