Hydrogen Bromide → 2-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

HRID 2268959노트

반응식

HRID 2268959 반응식
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH:17]([NH:19][C:20]2[N:25]=[C:24]([N:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]=[CH:27]3)[CH:23]=[CH:22][N:21]=2)[CH3:18])[CH2:12]1)=O)C1C=CC=CC=1.Br>C(Cl)Cl.C(O)(=O)C>[NH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH:17]([NH:19][C:20]2[N:25]=[C:24]([N:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]=[CH:27]3)[CH:23]=[CH:22][N:21]=2)[CH3:18])[CH2:12]1

참가 물질

5

반응물 2

HCID 260Hydrogen BromideHCID 155505842-[1-(1-Benzyloxycarbonylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

생성물 1

HCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine수율 85.5%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

The 2-[1-(1-benzyloxycarbonylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (900 mg, 1.97 mmol) was dissolved in CH2Cl2 (25 mL), and the mixture was cooled down to 0° C. To this was added 30% HBr in acetic acid (5 mL) slowly and continued stirring at 0° C. for 15 min The bath was removed, and the reaction mixture was stirred at room temperature for 45 min and then was diluted with H2O (25 mL). The reaction mixture was extracted with CH2Cl2 (2×20 mL; discarded), then the aqueous layer was made neutral with 5N NaOH and extracted with EtOAc (3×25 mL; discarded). The aqueous layer was made strongly basic (>pH 12) with SN NaOH, and was extracted with EtOAc (4×30 mL). The combined extracts were washed with brine and dried over Na2SO4. After removal of solvent under reduced pressure, 543 mg of the title compound was obtained which was used without purification. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.36 (br s, 1H); 8.16 (d, J=8 Hz, 1H); 7.85 (d, J=8.5 Hz, 1H); 7.38 (m, 2H); 6.75 (d, J=5.4 Hz, 1H); 5.14 (s, 2H); 4.1 (m, 1H); 3.18 (d, J=12 Hz, 1H); 3.02 (d, J=12 Hz, 1H); 1.23 (d, J=6.6 Hz, 3H).

후처리

  1. customwas removed
  2. stirringthe reaction mixture was stirred at room temperature for 45 min
  3. additionwas diluted with H2O (25 mL)
  4. extractionThe reaction mixture was extracted with CH2Cl2 (2×20 mL; discarded)
  5. extractionextracted with EtOAc (3×25 mL; discarded)
  6. extractionwas extracted with EtOAc (4×30 mL)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. customAfter removal of solvent under reduced pressure

출처 및 근거

ORD 기록
ord-1770ccd01eba42ec8d665ba36c703778
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329380B1

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