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 524218Notes

Reaction equation

HRID 524218 reaction equation
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

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-41bec9e6375a42d99ea2e444d3c03f07
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

Loading…