N-Hydroxyacetamidine → 5-(4-Iodo-2-methoxyphenyl)-3-methyl-1,2,4-oxadiazole

HRID 272700노트

반응식

HRID 272700 반응식
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.CN(C(O[N:21]1N=N[C:23]2C=CC=[N:27][C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(=NO)(N)C>CN(C=O)C>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:8][N:27]=[C:22]([CH3:23])[N:21]=2)=[C:4]([O:11][CH3:12])[CH:3]=1

참가 물질

7

반응물 5

HCID 30926N-HydroxyacetamidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 134507564-Iodo-2-methoxybenzoic acid

생성물 1

HCID 692184875-(4-Iodo-2-methoxyphenyl)-3-methyl-1,2,4-oxadiazole수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-iodo-2-methoxy benzoic acid (83 mg, 0.3 mmol), HATU (114 mg, 0.3 mmol), DIEA (26 μL, 0.15 mmol), and HOBt (8 mg, 0.06 mmol) in DMF was stirred at room temperature for 5 minutes. Acetamide oxime (22 mg, 0.3 mmol) was added, and reaction was stirred for 30 minutes at room temperature. The reaction was then heated to 110° C. for 16 hours. Cooled to room temperature. Partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by HPLC to provide 37 mg (39%) of desired product. MS (ESI) m/e 317 (M+H)+, 1H NMR (300 MHz, DMSO-d6): □ 7.70 (d, J=8.14 Hz, 1H), 7.64 (d, J=1.36 Hz, 1H), 7.53 (dd, J=8.31-1.53 Hz, 1H), 3.94 (s, 3H), 2.40 (s, 3H).

후처리

  1. customreaction
  2. stirringwas stirred for 30 minutes at room temperature
  3. temperatureThe reaction was then heated to 110° C. for 16 hours
  4. temperatureCooled to room temperature
  5. customPartitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-4ce947c228d14b578fb09dc10cdefc76
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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