Cvt-2738 → HCID 86619160, compound

HRID 1060198Notes

Reaction equation

HRID 1060198 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][C:10](=O)[CH2:9]1)=[O:7].[CH3:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[C:32]=1[NH:38][C:39](=[O:47])[CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>CO.[Pd]>[F:28][C:2]([F:1])([F:29])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:25])([F:27])[F:26])[CH:23]=1)[C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][C@H:10]([N:44]2[CH2:45][CH2:46][N:41]([CH2:40][C:39]([NH:38][C:32]3[C:33]([CH3:37])=[CH:34][CH:35]=[CH:36][C:31]=3[CH3:30])=[O:47])[CH2:42][CH2:43]2)[CH2:9]1)=[O:7]

Participants

5

Reactant 2

HCID 2608606Cvt-2738HCID 18630857HCID 18630857, compound

Product 1

HCID 86619160HCID 86619160, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-1-[3,5-bis(trifluoromethyl)benzoyl]-5-(phenylmethyl)-3-pyrrolidinone (0.0037 mol) and N-(2,6-dimethylphenyl)-1-piperazineacetamide (0.0037 mol) in methanol (150 ml) was hydrogenated at 50° C. with palladium on activated carbon (10%, 1 g) as a catalyst in the presence of tiophene solution (1 ml). After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The desired fractions were collected and the solvent was evaporated. The residue was dried and then crystallized from DIPE. The precipitate was filtered off and dried, yielding 0.35 g (15%) of (±)-cis-4-[1-[3,5-bis(trifluoromethyl)benzoyl]-5-(phenylmethyl)-3-pyrrolidinyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide (compound 131).

Workup

  1. filtrationAfter uptake of hydrogen, the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  4. customThe desired fractions were collected
  5. customthe solvent was evaporated
  6. customThe residue was dried
  7. customcrystallized from DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-66771ce4c15f451d89901d8b1f607621
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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