4-(6-Nitro-pyridin-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester → Tert-butyl 4-(6-aminopyridin-3-yl)-1,4-diazepane-1-carboxylate

HRID 2359537Notes

Reaction equation

HRID 2359537 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[N:17][C:18]([N+:21]([O-])=O)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 583154014-(6-Nitro-pyridin-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58315396Tert-butyl 4-(6-aminopyridin-3-yl)-1,4-diazepane-1-carboxylateYield 122.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By repeating procedures described in Example B, 4-(6-nitro-pyridin-3-yl)[1,4]diazepane-1-carboxylic acid tert-butyl ester (490 mg, 1.52 mmol) is hydrogenated over Pd—C on an H-cube (Thales) (instead of under an atmosphere of hydrogen) to give 4-(6-amino-pyridin-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (544 mg, 98%). MS (ESI) m/z 293 (M+H)+

Sources & evidence

ORD record
ord-534607a777c1412ca93ba797bb0d8c98
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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