1-Hydroxybenzotriazole → 7-(4-(1-imidazolyl)phenyl)-N-(4-((N-tetra-hydropyran-4-yl-N-methylamino)methyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

HRID 2228142ノート

反応式

HRID 2228142 の反応式
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[CH:14][C:15]4[O:21][CH2:20][CH2:19][C:18]([C:22](O)=[O:23])=[CH:17][C:16]=4[CH:25]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:26][N:27]([CH2:34][C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1)[CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.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>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[CH:14][C:15]4[O:21][CH2:20][CH2:19][C:18]([C:22]([NH:39][C:38]5[CH:40]=[CH:41][C:35]([CH2:34][N:27]([CH:28]6[CH2:33][CH2:32][O:31][CH2:30][CH2:29]6)[CH3:26])=[CH:36][CH:37]=5)=[O:23])=[CH:17][C:16]=4[CH:25]=3)=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 184726247-(4-(1-Imidazolyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

生成物 1

HCID 184724997-(4-(1-imidazolyl)phenyl)-N-(4-((N-tetra-hydropyran-4-yl-N-methylamino)methyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide収率 52.6%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 7—(4—(1-imidazolyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.13 g), 4—(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.11 g) and 1-hydroxybenzotriazole (0.07 g) in dimethylformamide (20 ml) was added 1-ethyl-3—(3-dimethylamino-propyl)carbodiimide hydrochloride (0.13 g) under ice-cooling. Under nitrogen atmosphere, the mixture was warmed to room temperature. To the mixture were added 4-dimethylaminopyridine (catalytic amount) and triethylamine (0.2 ml), and the mixture was stirred over night. The solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with 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/methanol/triethylamine) to give crude crystals, which were recrystallized from ethanol-hexane to give 7—(4—(1-imidazolyl)phenyl)-N-(4—((N-tetra-hydropyran-4-yl-N-methylamino)methyl)phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 153) (0.11 g) as pale yellow crystals.

後処理

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column (ethyl acetate/methanol/triethylamine)
  8. customto give crude crystals, which
  9. customwere recrystallized from ethanol-hexane

出典と根拠

ORDレコード
ord-0c3298cf5e324a55bdfed798fcc8372e
出典データセット
uspto-grants-2002_07
特許番号
US06413947B1

反応ノート

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