HCID 59936433, compound → HCID 69963261, compound

HRID 2228802Notes

Reaction equation

HRID 2228802 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5](=[O:21])[N:4]([CH2:22][C:23]([O:25]CC2C=CC=CC=2)=[O:24])[C:3]=1[CH3:33]>C(O)C.[OH-].[Pd+2].[OH-]>[ClH:1].[CH3:33][C:3]1[N:4]([CH2:22][C:23]([OH:25])=[O:24])[C:5](=[O:21])[C:6]([NH:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[N:7][CH:2]=1

Participants

4

Reactant 1

HCID 59936433HCID 59936433, compound

Product 1

HCID 69963261HCID 69963261, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 2-[3-chloro-2-methyl-6-oxo-5-({[(2R)-1-tetrahydro-2H-pyran-4-yl-2-pyrrolidinyl]methyl}amino)-1(6H)-pyrazinyl]acetate (preparation 158) (970 mg, 2.04 mmol) and palladium hydroxide (80 mg) in ethanol (8 ml) was hydrogenated at 15 psi and room temperature for 20 hrs. The reaction mixture was filtered through Whatman® fibre, and the filtrate evaporated under reduced pressure to give the desired compound, (680 mg, 95%). LRMS: m/z=351 (M+1)+.

Workup

  1. filtrationThe reaction mixture was filtered through Whatman® fibre
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e04dd32d4d744c1bd4a27943f4f158c
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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