Potassium Carbonate → Methyl 4-methyl-3-(3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate

HRID 541186노트

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HRID 541186 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:7]([O:9][CH3:10])=[O:8])(=[NH:3])[NH2:2].Br[CH:16]1[C:21](=O)[CH2:20][CH2:19][O:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[C:1]1[NH:2][C:16]2[CH2:17][O:18][CH2:19][CH2:20][C:21]=2[N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 222245413-Bromooxan-4-one2회HCID 68288326Methyl 3-carbamimidoyl-4-methylbenzoate2회

생성물 1

HCID 68289058Methyl 4-methyl-3-(3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate수율 39%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A mixture of methyl 3-carbamimidoyl-4-methylbenzoate (compound 1.9, 400 mg, 1.98 mmol, 1.00 equiv, 95%), 3-bromodihydro-2H-pyran-4(3H)-one (compound 1.10.1, 750 mg, 2.09 mmol, 1.00 equiv), and potassium carbonate (580 mg, 4.20 mmol, 2.00 equiv) in CH3CN (15 mL) was stirred overnight at 80° C. under nitrogen. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 50 mL of ethyl acetate and washed with 2×10 mL of H2O. The organic phase was dried over (Na2SO4) and concentrated under reduced pressure. The residue was purified using silica gel column chromatography and purified using ethyl acetate/petroleum ether (1/3) to yield 0.21 g (37%) of the title compound as a white solid.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 mL of ethyl acetate
  4. washwashed with 2×10 mL of H2O
  5. dry with materialThe organic phase was dried over (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. custompurified

출처 및 근거

ORD 기록
ord-5c97ef009abb4308a55aee8424e0fe71
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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