N'-(2-cyclopentyl-6-methoxy-pyridine-4-carbonyl)-hydrazinecarboxylic acid benzyl ester → 2-Cyclopentyl-6-methoxy-isonicotinic acid hydrazide

HRID 2278773Notes

Reaction equation

HRID 2278773 reaction equation
C(OC([NH:11][NH:12][C:13]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:16]=1)=[O:14])=O)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[CH:23]1([C:17]2[CH:16]=[C:15]([CH:20]=[C:19]([O:21][CH3:22])[N:18]=2)[C:13]([NH:12][NH2:11])=[O:14])[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 1

HCID 67491497N'-(2-cyclopentyl-6-methoxy-pyridine-4-carbonyl)-hydrazinecarboxylic acid benzyl ester

Product 1

HCID 674911922-Cyclopentyl-6-methoxy-isonicotinic acid hydrazideYield 90.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C (500 mg, 10% Pd) is added to a solution of N′-(2-cyclopentyl-6-methoxy-pyridine-4-carbonyl)-hydrazinecarboxylic acid benzyl ester (2.74 g, 7.42 mmol) in THF (50 mL) and methanol (50 mL). The mixture is stirred at rt under 1 bar of H2 for 25 h. The catalyst is removed by filtration and the filtrate is concentrated and dried under HV to give the title compound (1.58 g) as an off-white solid; LC-MS**: tR=0.51 min, [M+1]+=236.20; 1H NMR (D6-DMSO): δ 1.60-1.82 (m, 6H), 1.94-2.03 (m, 2H), 3.08-3.19 (m, 1H), 3.86 (s, 3H), 4.56 (s br, 2H), 6.93 (d, J=1.0 Hz, 1H), 7.20 (d, J=1.0 Hz, 1H), 9.94 (s, 1H).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. customdried under HV

Sources & evidence

ORD record
ord-03fc5323d6904d159951fc071ace2f7c
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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