Ammonium formate → 2-{1-[(5-Hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 1914146노트

반응식

HRID 1914146 반응식
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:44])=[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:32]=[C:33]([O:42][CH3:43])[C:34]5[O:38][C:37]([CH3:40])([CH3:39])[CH2:36][C:35]=5[CH:41]=4)=[N:24]3)[CH2:19][CH2:18]2)=[O:16])[CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:44])=[C:13]([C:15]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[C:27](=[O:28])[C:26]([CH3:30])([CH3:29])[C:25]([C:31]4[CH:32]=[C:33]([O:42][CH3:43])[C:34]5[O:38][C:37]([CH3:39])([CH3:40])[CH2:36][C:35]=5[CH:41]=4)=[N:24]3)[CH2:21][CH2:22]2)=[O:16])[CH:14]=1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 462023982-(1-{[5-(Benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

생성물 1

HCID 462023992-{1-[(5-Hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

Under a blanket of nitrogen 0.3 g of 2-(1-{[5-(benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 88) are dissolved in 20 ml of methanol and 0.04 g palladium on charcoal (10%) and 0.32 g ammonium formiate are added. The reaction mixture is heated to reflux or 4 h 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 purified by column chromatography (amino phase silica gel and DCM) to yield the title compound.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux or 4 h 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. customis purified by column chromatography (amino phase silica gel and DCM)

출처 및 근거

ORD 기록
ord-dd8f52e490044cee95286f1872ed6f91
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609848B2

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