Ethyl Acetate → HCID 71115218, 화합물

HRID 468964노트

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HRID 468964 반응식
[F:1][C@@H:2]1[CH2:4][C@@H:3]1[C:5]([OH:7])=O.CN(C(O[N:16]1N=N[C:18]2[CH:19]=[CH:20][CH:21]=[N:22][C:17]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:35]([CH2:39][CH3:40])[CH:36]([CH3:38])C)(C)C.C(O[CH2:45][CH3:46])(=O)C>CN(C=O)C>[F:1][C@@H:2]1[CH2:4][C@@H:3]1[C:5]([NH:16][C:17]1[N:22]=[CH:21][C:20]2[C:19]([CH:18]=1)=[CH:17][N:22]=[C:21]([C:40]1[CH:39]=[N:35][CH:36]=[CH:38][C:45]=1[CH3:46])[CH:20]=2)=[O:7]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10011855(1R,2R)-2-fluorocyclopropane-1-carboxylic acid

생성물 1

HCID 71115218HCID 71115218, 화합물수율 46%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

A mixture of (1R,2R)-2-fluorocyclopropanecarboxylic acid (35 mg, 0.34 mmol), HATU (139 mg, 0.36 mmol), and N,N-diisopropylethylamine (89 mg, 0.68 mmol) in DMF (1 mL) was heated at 70° C. for 8 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (25 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by reverse phase HPLC purification (5-85% ACN in water w/0.1% NH4OH, 14 min). Desired fractions were combined and evaporated in vacuo to afford the title compound as an off-white solid (25 mg, 46%). 1H NMR (400 MHz, DMSO) δ 11.20 (s, 1H), 9.50 (s, 1H), 9.34 (s, 1H), 8.68 (s, 1H), 8.68 (s, 1H), 8.50 (d, J=5.0 Hz, 1H), 8.19 (s, 1H), 7.39 (d, J=5.0 Hz, 1H), 5.08-4.85 (m, 1H), 2.44 (s, 3H), 2.30 (m, 1H), 1.72 (m, 1H), 1.23 (m, 1H). LCMS (Method E): RT=3.166 min, M+H+=323.2.

후처리

  1. washwashed with water (25 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue that
  7. customwas purified by reverse phase HPLC purification (5-85% ACN in water w/0.1% NH4OH, 14 min)
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-73da5e3d50e443fd9cb2456ec6597751
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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