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

HRID 565947노트

반응식

HRID 565947 반응식
N1(C2C=CC([C:13]3[CH:14]=[CH:15][C:16]4[O:22][CH2:21][CH2:20][C:19]([C:23](O)=[O:24])=[CH:18][C:17]=4[CH:26]=3)=CC=2)CCCCC1.C[N:28](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.C(N(CC)CC)C>[O:22]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:26][C:17]=2[CH:18]=[C:19]([C:23]([NH2:28])=[O:24])[CH2:20][CH2:21]1

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 184722357-(4-Piperidinophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

생성물 1

HCID 184723002,3-Dihydro-1-benzoxepine-4-carboxamide수율 221.6%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of 7-(4-piperidinophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.15g), 4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.1g) and 1hydroxy-benzotriazole (0.07g) in dimethylformamide (10ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.13g) under ice-cooling. Under nitrogen atmosphere, the mixture was warmed to room temperature. To the mixture were added 4-dimethylaminopyridine (catalytic amount) and triethylamine (0.18ml), and the mixture was stirred over night. The solvent was evaporated, and to the residue was added water. The mixture was 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 to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7-(4-piperidinophenyl)-N-(4-((N-methyl-N-tetrahydro-pyran-4-yl)amino)-methyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 151) (0.18g) as colorless crystals.

후처리

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. additionto the residue was added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. customto give crude crystals, which
  9. customwere recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-5a6dd8317d9e42a58aee36a4e5307869
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172061B2

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