Methyl 2-amino-4-{1-[(benzyloxy)carbonyl]-3-piperidinyl}-6-(2-hydroxyphenyl)nicotinate → 6-Amino-4-(2-hydroxy-phenyl)-5,9-diaza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one

HRID 412266Notes

Reaction equation

HRID 412266 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[CH:9]=[C:8]([CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25](OCC3C=CC=CC=3)=[O:26])[CH2:20]2)[C:3]=1C(OC)=O>CO.C1COCC1.[Pd]>[NH2:1][C:2]1[C:3]2[C:25](=[O:26])[N:21]3[CH2:20][CH:19]([CH2:24][CH2:23][CH2:22]3)[C:8]=2[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[N:11]=1

Participants

5

Reactant 1

HCID 136050638Methyl 2-amino-4-{1-[(benzyloxy)carbonyl]-3-piperidinyl}-6-(2-hydroxyphenyl)nicotinate

Product 1

HCID 1360506736-Amino-4-(2-hydroxy-phenyl)-5,9-diaza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-oneYield 41.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-amino-4-{1-[(benzyloxy)carbonyl]-3-piperidinyl}-6-(2-hydroxyphenyl)nicotinate (60 mg, 0.130 mmol) in methanol (2.0 mL) and THF (1.0 mL) was added 10% Pd—C (200 mg). The mixture was stirred at room temperature under a hydrogen atmosphere (1 atm) for 6.5 hrs. The mixture was filtrated on Celite®, and washed with MEOH and THF successively. The filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate, 2:1) to give 6-amino-4-(2-hydroxy-phenyl)-5,9-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one as a yellow solid (16 mg, yield; 40%).

Workup

  1. filtrationThe mixture was filtrated on Celite®
  2. washwashed with MEOH and THF successively
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative TLC (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-b8893db4edde4f838cb88475dc70687f
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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