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1-Hydroxybenzotriazole → N-(3-Bromo-4-fluorobenzyl)-1-methyl-N-(tetrahydro-2H-thiopyran-4-yl)-1H-imidazole-4-carboxamide

HRID 467957
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HRID 467957 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

HCID 58049379N-(3-Bromo-4-fluorobenzyl)-1-methyl-N-(tetrahydro-2H-thiopyran-4-yl)-1H-imidazole-4-carboxamide수율 66.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fd1f98e4a9454810bee3a7bd93a85dda
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08623898B2

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