Oxalyl chloride → (E)-4,4,5,5-tetrafluoro-N-[2-[[2-methyl-6-(2-methylbutoxy)-4-pyridyl]amino]ethyl]-pent-2-enamide

HRID 333076ノート

反応式

HRID 333076 の反応式
[F:1][C:2]([F:11])([CH:8]([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:18][C:19]1[CH:24]=[C:23]([NH:25][CH2:26][CH2:27][NH2:28])[CH:22]=[C:21]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[N:20]=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[F:11][C:2]([F:1])([CH:8]([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:28][CH2:27][CH2:26][NH:25][C:23]1[CH:22]=[C:21]([O:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH3:33])[N:20]=[C:19]([CH3:18])[CH:24]=1)=[O:7]

参加物

7

反応物 3

HCID 65578Oxalyl chlorideHCID 66835336N-[2-Methyl-6-(2-methylbutoxy)-4-pyridyl]ethane-1,2-diamineHCID 86691165(E)-4,4,5,5-tetrafluoropent-2-enoic acid

生成物 1

HCID 86691167(E)-4,4,5,5-tetrafluoro-N-[2-[[2-methyl-6-(2-methylbutoxy)-4-pyridyl]amino]ethyl]-pent-2-enamide収率 39%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(E)-4,4,5,5-tetrafluoropent-2-enoic acid (21 mg, 0.12 mmol) was dissolved in DCM (1 ml), oxalyl chloride was added (10 μl, 0.12 mmol) followed by a drop of DMF. The mixture was stirred for 10 minutes at room temperature. N-[2-methyl-6-(2-methylbutoxy)-4-pyridyl]-ethane-1,2-diamine (18 mg, 0.1 mmol) was dissolved in DMF (0.5 ml), the mixtures were combined, TEA (42 μl, 0.3 mmol) was added and the resulting mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 13 mg of a white solid (0.039 mmol, 39%).

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. washwashed with water and saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

出典と根拠

ORDレコード
ord-8260f32ef9a2436cb6fe49cb3ede1aa6
出典データセット
uspto-grants-2014_11
特許番号
US08877934B2

反応ノート

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