1-Hydroxybenzotriazole → 2,3-Dihydro-1-benzoxepine-4-carboxamide

HRID 1277222노트

반응식

HRID 1277222 반응식
C1OC2C=CC([C:10]3[CH:11]=[CH:12][C:13]4[O:19][CH2:18][CH2:17][C:16]([C:20](O)=[O:21])=[CH:15][C:14]=4[CH:23]=3)=CC=2O1.C[N:25](CC1C=CC(N)=CC=1)C1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.CN(C)C1C=CN=CC=1.O.C(N(CC)CC)C>[O:19]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:23][C:14]=2[CH:15]=[C:16]([C:20]([NH2:25])=[O:21])[CH2:17][CH2:18]1

참가 물질

9

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 184722047-(3,4-Methlenedioxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

생성물 1

HCID 184723002,3-Dihydro-1-benzoxepine-4-carboxamide수율 222.6%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of 7-(3,4-methlenedioxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.14 g), 4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.11 g) and 1-hydroxy-benzotriazole (0.15 g) in dimethylformamide (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.13 g) under ice-cooling. Under nitrogen atmosphere, the reaction mixture was warmed to room temperature. To the mixture were added 4-dimethylaminopyridine (3 mg) and triethylamine (0.19 ml), and the mixture was stirred for 18 hours, poured into water, and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate) to give 7-(3,4-methlenedioxyphenyl)-4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.19 g).

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column (ethyl acetate)

출처 및 근거

ORD 기록
ord-d295db1188914547af7fc4e9409a3662
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166006

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