HCID 57509941, compound → HCID 57510019, compound

HRID 624244Notes

Reaction equation

HRID 624244 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:11]>CO.O1CCCC1.[Pd]>[NH:22]1[CH2:21][CH2:20][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10]([N:2]3[CH2:3][C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:1]3)=[O:11])=[CH:14][CH:15]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 1

HCID 57509941HCID 57509941, compound

Product 1

HCID 57510019HCID 57510019, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

tert-Butyl 4-(4-(isoindoline-2-carboxamido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (1.00 g, 2.38 mmol) in 20 ml of 1:1 methanol/tetrahydrofuran was added to 5% Pd on carbon (wet) (0.200 g) in a 50 ml pressure bottle and stirred for 16 hours at 30 atm and room temperature. The mixture was filtered through a nylon membrane and concentrated. The residue was suspended in dichloromethane, stirred 1 hour and filtered with dichloromethane washes to provide the title compound.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. stirringstirred 1 hour
  4. filtrationfiltered with dichloromethane

Sources & evidence

ORD record
ord-ad1f7309d07147818e434a23e4d0d842
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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