Ammonium formate → HCID 59591434, 화합물

HRID 1963003노트

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HRID 1963003 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[C:13]([F:23])=[C:14]([C:19](=[N:21]O)[NH2:20])[C:15]([F:18])=[CH:16][CH:17]=3)=[N:7][C:6]=2[CH:24]=1.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[C:13]([F:23])=[C:14]([C:19](=[NH:20])[NH2:21])[C:15]([F:18])=[CH:16][CH:17]=3)=[N:7][C:6]=2[CH:24]=1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 72334044HCID 72334044, 화합물

생성물 1

HCID 59591434HCID 59591434, 화합물수율 21%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

A mixture of 3-[(5-chloro-1,3-benzothiazol-2-yl)methoxy]-2,6-difluoro-N′-hydroxybenzenecarboximidamide (156, mg, 0.42 mmol, 1 equiv.), 10% Pd/C (63 mg) and ammonium formate (133 mg, 2.1 mmol, 5 equiv.) in glacial acetic acid (2 ml) was stirred under reflux for 3 h. The mixture was filtered through a pad of celite, alkalised to pH 10 with 0.5N NaOH and extracted with EtOAc (3×15 ml). The combined organic extracts were dried (MgSO4) and evaporated to dryness under reduced pressure. The crude residue was dissolved in DMSO and precipitated by addition of H2O. The solid was filtered, washed with H2O and pentane, to give 49 mg (33% yield). Purity 62% by HPLC (Gemini C18, 50×4.6 mm): m/z 354 [M+H]+, Rt=3.09 min. HPLC-MS analysis suggested that there was also 6% un-reacted starting material and 21% of the title compound without the Cl atom.

후처리

  1. temperatureunder reflux for 3 h
  2. filtrationThe mixture was filtered through a pad of celite
  3. extractionextracted with EtOAc (3×15 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated to dryness under reduced pressure
  6. dissolutionThe crude residue was dissolved in DMSO
  7. customprecipitated by addition of H2O
  8. filtrationThe solid was filtered
  9. washwashed with H2O and pentane
  10. customto give 49 mg (33% yield)
  11. customun-reacted

출처 및 근거

ORD 기록
ord-d7b06d4f0ac046658ff1923a7f7cb8d2
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415383B2

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