Diisopropylamine → 2-Chloro-6-(2-hydroxybutylamino)-4-(trifluoromethyl)pyridine-3-carbonitrile

HRID 1911821ノート

反応式

HRID 1911821 の反応式
[C:1]([C:3]1[C:4]([Cl:14])=[N:5][C:6](Cl)=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])#[N:2].N[CH:16]([CH2:19]C)[CH2:17][OH:18].[CH:21]([NH:24]C(C)C)(C)C.ClCl>>[Cl:14][C:4]1[C:3]([C:1]#[N:2])=[C:8]([C:9]([F:12])([F:11])[F:10])[CH:7]=[C:6]([NH:24][CH2:21][CH:17]([OH:18])[CH2:16][CH3:19])[N:5]=1

参加物

5

反応物 4

HCID 7912DiisopropylamineHCID 221292-Amino-1-butanolHCID 24526ChlorineHCID 27367262,6-Dichloro-4-(trifluoromethyl)nicotinonitrile

生成物 1

HCID 866534212-Chloro-6-(2-hydroxybutylamino)-4-(trifluoromethyl)pyridine-3-carbonitrile収率 55%

実験手順

Neat 3-cyano-2,6-dichloro-4-trifluoromethylpyridine (0.641 g, 6 mmol) was added by pipette at a dropwise rate over 3 minutes to 2-aminobutanol (1.5 g, 6 mmol). Di-isopropylamine (0.9 g, 7 mmol) was added after 10 minutes and the resultant mixture was heated in a sealed tube at 70° C. for 30 minutes to selectively displace the chlorine at position 6 before quenching in ice-cold water and extracted with dichloromethane. Organic extracts were washed twice with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was washed with diethylether and the resultant solid was used in the next step without further purification. 2-Chloro-6-(2-hydroxybutylamino)-4-(trifluoromethyl) pyridine-3-carbonitrile was isolated in 55% yield.

後処理

  1. custombefore quenching in ice-cold water
  2. extractionextracted with dichloromethane
  3. washOrganic extracts were washed twice with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with diethylether
  7. customthe resultant solid was used in the next step without further purification

出典と根拠

ORDレコード
ord-fad227854cef4529aa8948823934ee13
出典データセット
uspto-grants-2013_12
特許番号
US08604199B2

反応ノート

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