Triethylamine → HCID 59354919、化合物

HRID 1099437ノート

反応式

HRID 1099437 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[F:46][C:47]([F:52])([F:51])[CH2:48][CH2:49][NH2:50]>C(#N)C>[F:46][C:47]([F:52])([F:51])[CH2:48][CH2:49][NH:50][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][N:9]=1)=[O:13]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252105053,3,3-Trifluoropropylamine hydrochloride

生成物 1

HCID 59354919HCID 59354919、化合物収率 25%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

5-(methoxycarbonyl)pyridine-2-carboxylic acid (100 mg, 0.55 mmol) was dissolved in acetonitrile (1 mL). Triethylamine (0.230 mL, 1.66 mmol) and O-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (314 mg, 0.83 mmol) were added. The reaction mixture was stirred at rt for 5 min. 3,3,3-trifluoropropylamine hydrochloride (83 mg, 0.55 mmol) was added and the reaction mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo and the crude was pardoned between ethyl acetate and 1M sodium hydroxide. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude was purified by column chromatography using a gradient of ethyl acetate in heptane yielded 38 mg (25%) of the title compound as a white solid; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.17 (t, 1 H), 9.11 (d, 1 H), 8.48 (dd, 1 H), 8.18 (d, 1 H), 3.92 (s, 3 H), 3.53-3.60 (m, 2 H), 2.54-2.66 (m, 2 H); MS (ESI) m/z 277[M+H+], m/z 275[M−H+];

後処理

  1. stirringthe reaction mixture was stirred at ambient temperature for 2 h
  2. customThe solvent was removed in vacuo
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-318c1becbabf4afdbf5581d0337ba3b8
出典データセット
uspto-grants-2012_03
特許番号
US08143408B2

反応ノート

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