Dichloromethane → Tert-butyl cis-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

HRID 1620044ノート

反応式

HRID 1620044 の反応式
ClC(Cl)(Cl)C(Cl)=O.ClCCl.[NH2:11][C:12]([C:14]1[CH:15]=[C:16]([F:36])[C:17]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:18][C:19]=1[Cl:20])=O>C(N(CC)CC)C>[Cl:20][C:19]1[N:18]=[C:17]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:32])[CH3:33])[C:16]([F:36])=[CH:15][C:14]=1[C:12]#[N:11]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 6420Trichloroacetyl chlorideHCID 86683847Tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

生成物 1

HCID 86683848Tert-butyl cis-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate収率 76%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

Trichloroacetyl chloride (0.55 ml) was added dropwise to a dichloromethane (17 ml) suspension containing tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (1.74 g) and triethylamine (1.38 ml) under ice cooling, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, and a saturated aqueous ammonium chloride solution and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0 to 3:1), diisopropylether was added, solid matter was collected by filtration, and a white solid of tert-butyl cis-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (1.26 g) was thus obtained.

後処理

  1. distillationThe solvent was distilled away under reduced pressure
  2. additiona saturated aqueous ammonium chloride solution and ethyl acetate were added
  3. customThe organic layer was collected
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0 to 3:1), diisopropylether
  8. additionwas added
  9. filtrationsolid matter was collected by filtration

出典と根拠

ORDレコード
ord-bfd60118006945598c10c16609d792b1
出典データセット
uspto-grants-2014_07
特許番号
US08772320B2

反応ノート

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