HCID 70980218, compound → HCID 70980115, compound

HRID 1749098Notes

Reaction equation

HRID 1749098 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[C:21]([C:28]#[N:29])[N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:30])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH2:28][NH2:29])[N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 70980218HCID 70980218, compound

Product 1

HCID 70980115HCID 70980115, compoundYield 130.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-cyano-5-nitro-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (1.06 g, 2.56 mmol) in THF (10 mL) and acetic acid (20 mL) was added Pd/C (10%, 200 mg) and the reaction mixture was hydrogenated overnight. The catalyst was filtered and the filtrate evaporated to afford (5-amino-6-aminomethyl-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (1.3 g) as the acetate salt, which was used without further purification. MS: [M+H]+=389.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-6487a230ede24728876282e286c9d244
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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