Hexamethylenetetramine → 6-Cyclopropoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

HRID 1244020노트

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HRID 1244020 반응식
[C:1]([OH:7])([C:3](F)(F)F)=O.C1N2CN3CN(C2)CN1C3.[CH:18]1([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30]C=2)[N:28]([CH3:32])[C:27](=[O:33])[CH2:26][CH2:25]3)[CH2:20][CH2:19]1>>[CH:18]1([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][C:3]=2[CH:1]=[O:7])[N:28]([CH3:32])[C:27](=[O:33])[CH2:26][CH2:25]3)[CH2:20][CH2:19]1

참가 물질

4

반응물 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acid2회HCID 219318836-Cyclopropoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one

생성물 1

HCID 219317736-Cyclopropoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde수율 37%

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온도
65 °C

실험 절차

TFA (1.38 ml) solution of hexamethylenetetramine (58 mg, 0.42 mmol) was heated to 70° C. for 1 hour under nitrogen. Another TFA (0.69 ml) solution of 6-Cyclopropoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (30 mg, 0.138 mmol) was then added to the above at room temperature and the reaction mixture was heated to 65° C. for an overnight. It was then cooled to room temperature, quenched with water and extracted with ethyl acetate (30 ml). The combined fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was chromatographed using 40% ethylacetate/hexane to yield the title compound as a solid (13 mg, 37% yield). 1H NMR (400 MHz, CDCl3) δ 0.84–0.87 (4H, m), 2.64–2.267 (2H, m), 2.94–2.98 (2H, m), 3.35 (3H, s), 3.80–3.85 (1H, m), 7.17 (1H, s), 7.39 (1H, s), 10.33 (1H, s). m/z (APCI+) 246 (M+1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 μM, 125×4 mm column), 4.454 min.

후처리

  1. temperatureIt was then cooled to room temperature
  2. customquenched with water
  3. extractionextracted with ethyl acetate (30 ml)
  4. dry with materialThe combined fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-5c94cb972d4f4c1f8e35a9e07c54d858
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

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