Nitrogen → HCID 67951737, compound

HRID 1616808Notes

Reaction equation

HRID 1616808 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH:32]=2)[CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[CH:20]=[C:19]2[CH:24]([CH3:26])[CH3:25])=[O:13].[H][H].N#N>C(O)C.[Pd].C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:31][CH2:32]2)[CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[CH:20]=[C:19]2[CH:24]([CH3:26])[CH3:25])=[O:13]

Participants

7

Reactant 3

HCID 947NitrogenHCID 67818391HCID 67818391, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67951737HCID 67951737, compoundYield 103.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-[7-({[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1-methyl-3-(1-methylethyl)-1H-indol-5-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate (0.27 g, 0.507 mmol) was dissolved in ethanol (10 mL) and placed in a funnel under a N2 stream for 10 min. Palladium on carbon (0.081 g, 0.076 mmol) was added and the reaction placed alternatingly under N2 and H2 via a 3-way valve. Switched atmosphere to hydrogen (balloon) and stirred at RT overnight. Placed reaction back under N2, diluted with DCM, and added Celite. The mixture was stirred for 5 min, then filtered through analytical grade Celite and washed with 10% MeOH. Solvent was removed in vacuo giving a residue that was dried on hi-vacuum for 1 h to give 1,1-dimethylethyl 4-[7-({[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1-methyl-3-(1-methylethyl)-1H-indol-5-yl]-1-piperidinecarboxylate (0.28 g, 0.524 mmol, 103% yield). MS (ES) [M+H]+ 535.0.

Workup

  1. customplaced in a funnel under a N2
  2. additionadded Celite
  3. filtrationfiltered through analytical grade Celite
  4. washwashed with 10% MeOH
  5. customSolvent was removed in vacuo
  6. customgiving a residue that
  7. customwas dried on hi-vacuum for 1 h

Sources & evidence

ORD record
ord-c8058b671e80427bad2009fe64564d91
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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