N-methyl-N-phenyl-hydrazine → 5-(Tetrahydro-pyran-4-yl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid N'-methyl-N'-phenyl-hydrazide

HRID 240739

反応式

HRID 240739 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:9][CH:10]=[C:11]([CH:15]=2)[C:12]([OH:14])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:53][N:54]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[NH2:55]>CN(C=O)C.O1CCCC1>[CH3:53][N:54]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[NH:55][C:12](=[O:14])[C:11]1[CH:15]=[C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[C:8]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:9][CH:10]=1

参加物

7

反応物 4

HCID 36299N-methyl-N-phenyl-hydrazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 712941565-(Tetrahydro-pyran-4-yl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid

生成物 1

HCID 712941975-(Tetrahydro-pyran-4-yl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid N'-methyl-N'-phenyl-hydrazide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 10 mL two-necked flask, the above prepared 5-(tetrahydro-pyran-4-yl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (50 mg, 164 μmol, Eq: 1.00) was combined with tetrahydrofuran (1.0 mL) and DMF (1 mL) to give a colorless solution. TBTU (78.9 mg, 246 μmol, Eq: 1.5) and N,N-diisopropylethylamine (106 mg, 143 μl, 819 μmol, Eq: 5) were added and the reaction mixture stirred for 10 min at rt before 1-methyl-1-phenylhydrazine (24.0 mg, 23.1 μl, 197 μmol, Eq: 1.2, CAN 618-40-6) was added and the reaction mixture kept overnight at rt. Work up: The reaction mixture was quenched with 1 M HCl (10 mL) and extracted with EtOAc (2×20 mL). The organic layers were washed with 1 M NaOH, then with H2O/NaCl sol., the combined organic layers were dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (silica gel, 10 g, 15% to 50% EtOAc in heptane) delivered eventually 62 mg of the title compound as white foam; MS (EI) 410.2 (M+H)+.

後処理

  1. customto give a colorless solution
  2. additionwas added
  3. customThe reaction mixture was quenched with 1 M HCl (10 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. washThe organic layers were washed with 1 M NaOH
  6. dry with materialwith H2O/NaCl sol., the combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (silica gel, 10 g, 15% to 50% EtOAc in heptane)

出典と根拠

ORDレコード
ord-aece1061b8a64810b243acde6c6c4d60
出典データセット
uspto-grants-2014_02
特許番号
US08648099B2

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