Phosphorus sulfide (P2S5) → 4-[5-Fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-thiocarboxamide

HRID 1418466노트

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HRID 1418466 반응식
[F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2([C:14]([NH2:16])=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:32].C(=O)(O)[O-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2([C:14](=[S:32])[NH2:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1

참가 물질

5

반응물 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 9931329CJ-13454

생성물 1

HCID 187863764-[5-Fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-thiocarboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

To a stirred solution of 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]-phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide (Example 5) in THF (10 ml) was added phosphorus pentasulfide (236 mg, 0.53 mmol) and sodium bicarbonate (176 mg, 2.1 mmol). The resulting mixture was heated at 40° C. for 4 hr. The mixture was concentrated in vacuo. To the residue was added water (100 ml) and the mixture was extracted with dichloromethane (2×100 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified on column chromatography (LiChropprep --NH2) and then by p-TLC eluting with dichloromethane-methanol (10:1) to afford 38 mg of the titled compound as white solids.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added water (100 ml)
  3. extractionthe mixture was extracted with dichloromethane (2×100 ml)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on column chromatography (LiChropprep --NH2)
  7. washby p-TLC eluting with dichloromethane-methanol (10:1)

출처 및 근거

ORD 기록
ord-fd6b0df827d742aba641db8be8f1f584
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883106

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