4-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine → HCID 178434522, 화합물

HRID 888614노트

반응식

HRID 888614 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([CH3:44])=[N:22][N:23](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:24]=4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>Cl.C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([CH3:44])=[N:22][NH:23][CH:24]=4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 1

HCID 672351344-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine

생성물 1

HCID 178434522HCID 178434522, 화합물

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of 4-(4-chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine (178 mg, 0.30 mmol) in 5N hydrochloric acid (5 mL), THF (5 mL) and methanol (5 mL) was stirred for 140 minutes. The organic solvents were removed in vacuo then the resulting solution was diluted with 2N HCl and washed with ether. The aqueous phase was basified by addition of sodium hydroxide pellets then extracted with ethyl acetate. This organic extract was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with a gradient of 2M ammonia in methanol (5% to 7.5%) and dichloromethane. The product was further purified by preparative HPLC to give the title compound which was converted to its dihydrochloride salt (84 mg, 80%); LCMS (PS-A3) Rt 6.86 min [M+H]+ 352. 1H NMR (Me-d3-OD) δ 2.55 (3H, s), 2.70-2.75 (4H, m), 3.22-3.27 (4H, m), 7.35-7.41 (4H, m), 7.47-7.54 (4H, m), 8.32 (2H, s).

후처리

  1. customThe organic solvents were removed in vacuo
  2. additionthe resulting solution was diluted with 2N HCl
  3. washwashed with ether
  4. additionThe aqueous phase was basified by addition of sodium hydroxide pellets
  5. extractionthen extracted with ethyl acetate
  6. extractionThis organic extract
  7. washwas washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a residue which
  12. customwas purified by column chromatography (SiO2)
  13. washeluting with a gradient of 2M ammonia in methanol (5% to 7.5%) and dichloromethane
  14. customThe product was further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-bbb4b02e4dc940aca17b2e55969f4314
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247576B2

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