Acetic Acid → HCID 136050744, compound

HRID 412257Notes

Reaction equation

HRID 412257 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([O:29]CC3C=CC=CC=3)=[CH:27][CH:26]=[CH:25][C:24]=2[O:37]CC2C=CC=CC=2)[N:3]=1.C(O)(=O)C>C(OCC)(=O)C.C1COCC1.[Pd]>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=2[OH:37])[N:3]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 22258874HCID 22258874, compound

Product 1

HCID 136050744HCID 136050744, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of tert-butyl 3-{2-amino-6-[2,6-bis(benzyloxy)phenyl]-3-cyano-4-pyridinyl}-1-piperidinecarboxylate (3.46 g, 5.9 mmol) and Pd/C (10%, 600 mg) in ethyl acetate (50 mL) including acetic acid (5 mL) was stirred for 2 days at room temperature under a hydrogen atmosphere. The reaction mixture was diluted with THF (200 mL) and filtered through Celite®. The filtrate was concentrated under reduced pressure. The residue was washed with ethyl acetate and hexane, and dried under reduced pressure to give tert-butyl 3-[2-amino-3-cyano-6-(2,6-dihydroxy-phenyl)-4-pyridinyl]-1-piperidinecarboxylate (1.82 g, yield; 76%).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. washThe residue was washed with ethyl acetate and hexane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-9bd18aeab68441ae9b2620af170c9d09
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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