Ammonium formate → 5-(3,4-Dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524214노트

반응식

HRID 524214 반응식
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:41])=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:27](=[O:28])[C:26]([CH3:30])([CH3:29])[C:25]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=4)=[N:24]3)[CH2:19][CH2:18]2)=[O:16])[CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd].CC(=O)OCC>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([C:25]2[C:26]([CH3:30])([CH3:29])[C:27](=[O:28])[N:23]([CH:20]3[CH2:21][CH2:22][N:17]([C:15]([C:13]4[CH:14]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=4[CH3:41])=[O:16])[CH2:18][CH2:19]3)[N:24]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 462020662-(1-{[5-(Benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

생성물 1

HCID 462020675-(3,4-Dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

Under a blanket of nitrogen 4.0 g of 2-(1-{[5-(benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 84) are dissolved in 80 ml of methanol and 0.4 g palladium on charcoal (10%) and 2.25 g ammonium formiate are added. The reaction mixture is heated to reflux or 20 min until the starting material is consumed according to TLC analysis. The mixture is filtered over a plug of celite, and the solvent is removed under reduced pressure resulting in the crude product, which is taken up in EA and washed twice with water and with brine. Crystallization from EA and PE results in the title compound.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux or 20 min until the starting material
  3. customis consumed
  4. filtrationThe mixture is filtered over a plug of celite
  5. customthe solvent is removed under reduced pressure
  6. customresulting in the crude product, which
  7. washwashed twice with water and with brine
  8. customCrystallization from EA and PE

출처 및 근거

ORD 기록
ord-dc5a3b433eda4961a6a9285276063863
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340522B2

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