4-(4-Chloro-phenyl)-4-[4-(3-methyl-1-trityl-1H-pyrazol-4-yl)-phenyl]-piperidine → HCID 178434522、化合物

HRID 2361819ノート

反応式

HRID 2361819 の反応式
[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

参加物

5

反応物 1

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

生成物 1

HCID 178434522HCID 178434522、化合物

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2b3cc2d05cba47e4bf6eec783799fb9f
出典データセット
uspto-grants-2014_04
特許番号
US08691806B2

反応ノート

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