1-Hydroxybenzotriazole → HCID 58049379、化合物

HRID 467957

反応式

HRID 467957 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][CH:7]1[CH2:12][CH2:11][S:10][CH2:9][CH2:8]1.[CH3:17][N:18]1[CH:22]=[C:21]([C:23](O)=[O:24])[N:20]=[CH:19]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(N(CC)CC)C.CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]([CH:7]1[CH2:8][CH2:9][S:10][CH2:11][CH2:12]1)[C:23]([C:21]1[N:20]=[CH:19][N:18]([CH3:17])[CH:22]=1)=[O:24]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58049393N-(3-Bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine

生成物 1

HCID 58049379HCID 58049379、化合物収率 66.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

A mixture of N-(3-bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine (1.72 g), 1-methyl-1H-imidazole-4-carboxylic acid (0.71 g), EDC.HCl (1.63 g), HOBt (0.87 g), dimethylformamide (30 mL) and triethylamine (1.8 mL) was stirred overnight at room temperature. The solvent was distilled off under reduced pressure and after extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (1.55 g).

後処理

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionafter extraction with ethyl acetate
  3. washthe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtering off the desiccant
  6. concentrationthe solvent was concentrated
  7. customThe residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate)

出典と根拠

ORDレコード
ord-fd1f98e4a9454810bee3a7bd93a85dda
出典データセット
uspto-grants-2014_01
特許番号
US08623898B2

関連ノート

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