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

HRID 245085Notes

Reaction equation

HRID 245085 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-a223a2bf0d6e4e00a3da8c9f6e798ec7
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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