Diisopropylethylamine → 2-Bromo-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide

HRID 467959노트

반응식

HRID 467959 반응식
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[Br:20][C:21]1[N:22]([CH3:29])[CH:23]=[C:24]([C:26](O)=[O:27])[N:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:20][C:21]1[N:22]([CH3:29])[CH:23]=[C:24]([C:26]([N:8]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[C:4]([O:3][C:2]([F:18])([F:1])[F:19])[CH:5]=2)=[O:27])[N:25]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 510638082-Bromo-1-methyl-1H-imidazole-4-carboxylic acidHCID 58049381N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine

생성물 1

HCID 469166852-Bromo-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamide수율 57.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of N-[3-(trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (190 mg), 2-bromo-1-methyl-1H-imidazole-4-carboxylic acid (100 mg), HATU, diisopropylethylamine (190 mg) and acetonitrile (3 mL) was stirred overnight at room temperature. Acetonitrile was distilled off under reduced pressure and the residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=3:1 to 1:2) to give the titled compound (130 mg).

후처리

  1. distillationAcetonitrile was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=3:1 to 1:2)

출처 및 근거

ORD 기록
ord-d44b65a5676d4218840e159c902e3197
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623898B2

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