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

HRID 541186ノート

反応式

HRID 541186 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 222245413-Bromooxan-4-one2 回HCID 68288326Methyl 3-carbamimidoyl-4-methylbenzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5c97ef009abb4308a55aee8424e0fe71
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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