Ethyl Acetate → HCID 71115218, 화합물

HRID 1502480노트

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HRID 1502480 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

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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-2ce9b4c3a88440998429ca082ad5a0b4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206175B2

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