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Triethylamine → 2-[1-(1-Dimethylphosphonopiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]-pyrimidine

HRID 2268962
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HRID 2268962 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1.C(N(CC)CC)C.[P:32](Cl)([O:36][CH3:37])([O:34][CH3:35])=[O:33]>C(Cl)Cl.CCOC(C)=O>[CH3:35][O:34][P:32]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1)([O:36][CH3:37])=[O:33]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 101863Phosphorochloridic acid, dimethyl esterHCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

생성물 1

HCID 701386792-[1-(1-Dimethylphosphonopiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]-pyrimidine수율 69.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8857
Ethyl Acetate
용매

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온도
0 °C

실험 절차

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (44 mg, 0.136 mmol) in CH2Cl2 (1.5 mL) was added triethylamine (29 μL, 0.204 mmol) followed by dimethyl chlorophosphate (22 μL, 0.204 mmol) at 0° C. After stirring 30 min at 0° C., the reaction mixture was diluted with EtOAc (10 mL) and was washed with saturated aqueous NaHCO3 followed by brine. The organic layer was dried over Na2SO4. After removal of the solvent, the crude product was purified by preparative thin layer chromatography (3:1 acetone:hexane) to obtain 40.6 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.36 (br s, 1H); 8.14 (d, J=7.3 Hz, 1H); 7.83 (d, J=7.3 Hz, 1H); 7.38 (m, 2H); 6.78 (d, J=5.4 Hz, 1H); 4.15 (m, 1H); 3.67 (s, 3H); 3.65 (s, 3H); 1.28 (d, J=6.5 Hz, 3H). Mass spectrum 431.3 (ESI, M+1).

후처리

  1. washwas washed with saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customAfter removal of the solvent
  4. customthe crude product was purified by preparative thin layer chromatography (3:1 acetone:hexane)

출처 및 근거

ORD 기록
ord-11d3078afa6f454ca62ac06c036457be
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06329380B1

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