Triethylamine → HCID 59354919, 화합물

HRID 1099437노트

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HRID 1099437 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 59354919HCID 59354919, 화합물수율 25%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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+];

후처리

  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

출처 및 근거

ORD 기록
ord-318c1becbabf4afdbf5581d0337ba3b8
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143408B2

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